Are there amide versions of lactides and lactones?











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In my book, I read that Lactides and lactones are cyclic esters which contain two and one ester group in them, respectively. They are formed when $alpha$-hydroxy; and $gamma$- or $delta$- hydroxy carboxylic acids; respectively, are esterified.



Now, there exists a certain similarity between amides and esters (both being carboxylic acid-derivatives), such as the similarity between ester bonds in polyesters and amide bonds in polyamides.



In this context, I have a question: Do amides have compounds similar to lactides and lactones? What are they commonly known as?



Please let me know a good source that I could refer to in addition to any answers posted, or please cite any sources used.










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  • 1




    By the way, there are also lactols.
    – mykhal
    Nov 23 at 15:43















up vote
3
down vote

favorite












In my book, I read that Lactides and lactones are cyclic esters which contain two and one ester group in them, respectively. They are formed when $alpha$-hydroxy; and $gamma$- or $delta$- hydroxy carboxylic acids; respectively, are esterified.



Now, there exists a certain similarity between amides and esters (both being carboxylic acid-derivatives), such as the similarity between ester bonds in polyesters and amide bonds in polyamides.



In this context, I have a question: Do amides have compounds similar to lactides and lactones? What are they commonly known as?



Please let me know a good source that I could refer to in addition to any answers posted, or please cite any sources used.










share|improve this question


















  • 1




    By the way, there are also lactols.
    – mykhal
    Nov 23 at 15:43













up vote
3
down vote

favorite









up vote
3
down vote

favorite











In my book, I read that Lactides and lactones are cyclic esters which contain two and one ester group in them, respectively. They are formed when $alpha$-hydroxy; and $gamma$- or $delta$- hydroxy carboxylic acids; respectively, are esterified.



Now, there exists a certain similarity between amides and esters (both being carboxylic acid-derivatives), such as the similarity between ester bonds in polyesters and amide bonds in polyamides.



In this context, I have a question: Do amides have compounds similar to lactides and lactones? What are they commonly known as?



Please let me know a good source that I could refer to in addition to any answers posted, or please cite any sources used.










share|improve this question













In my book, I read that Lactides and lactones are cyclic esters which contain two and one ester group in them, respectively. They are formed when $alpha$-hydroxy; and $gamma$- or $delta$- hydroxy carboxylic acids; respectively, are esterified.



Now, there exists a certain similarity between amides and esters (both being carboxylic acid-derivatives), such as the similarity between ester bonds in polyesters and amide bonds in polyamides.



In this context, I have a question: Do amides have compounds similar to lactides and lactones? What are they commonly known as?



Please let me know a good source that I could refer to in addition to any answers posted, or please cite any sources used.







organic-chemistry esters amides






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asked Nov 23 at 6:09









AbhigyanC

956326




956326








  • 1




    By the way, there are also lactols.
    – mykhal
    Nov 23 at 15:43














  • 1




    By the way, there are also lactols.
    – mykhal
    Nov 23 at 15:43








1




1




By the way, there are also lactols.
– mykhal
Nov 23 at 15:43




By the way, there are also lactols.
– mykhal
Nov 23 at 15:43










2 Answers
2






active

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7
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Amide analogue of lactons are lactams, their tautomeric forms are lactims. Citing from the IUPAC Nomenclature of Organic Chemistry (Preferred names 2013):




P-66.1.5.1 Lactams and lactims



Intramolecular amides of amino carboxylic acids, $ce{-CO-NHbond{-}}$, are
called ‘lactams’ and their tautomers, $ce{-C(OH)=Nbond{-}}$, are ‘lactims’. Lactams named in two ways:



  (1) as heterocyclic pseudoketones;



  (2) by substituting ‘lactam’ for the ‘ic acid’ ending of the systematic ‘oic acid’ name for the parent acid without the amino substituent, and inserting a locant designating the position of the amino group between the ‘o’ and the ‘lactam’. Method ‘lactams’. Lactims are named in the same way, using ‘lactim’ in place of ‘lactam’.



(1) generates preferred IUPAC names.



Examples:



Fig.1



pyrrolidin-2-one (PIN)

butano-4-lactam



(…)



enter image description here



3,4,5,6-tetrahydropyridin-2-ol (PIN)

pentano-5-lactim




(Note that the numberings depicted are for the preferred names (PINs) based on nitrogen heterocyclics)



There's no (at least IUPAC) term for lactides analogue (‘lactide’ is not used in IUPAC names themselves anyway), but they exist.



In traditional or general names, the Greek letter numbering is used, e.g. ε-caprolactam, or β-lactam four-membered ring part in bicyclic penicillin skeleton.






share|improve this answer



















  • 2




    Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
    – Mathew Mahindaratne
    Nov 23 at 8:46






  • 1




    @MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
    – AbhigyanC
    Nov 23 at 11:21










  • @AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
    – Mithoron
    Nov 24 at 21:45


















up vote
0
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Cyclic amides are known as lactams. They can be a β-lactam which is a 4-membered ring, a γ-lactam which is a 5-membered ring, a δ-lactam which is a 6- membered ring, an ε-lactam which is 7-membered ring, and so on.
An example of a drug containing a β-lactam ring is ezetimibe. Antibiotics that contain a β-lactam ring are collectively known as β-lactam antibiotics which include penicillins such as amoxicillin, cephalosporins such as cephalexin, cephamycins such as cefoxitin, carbacephems such as loracarbef, carbapenems such as doripenem, monobactams such as aztreonam, oxacephems such as moxalactam.
Examples of drugs containing a γ-lactam ring include levetiracetam, doxapram, glimepiride.
Examples of drugs containing a δ-lactam ring include perampanel, milrinone, pirfenidone.
Example of a drug containing an ε-lactam ring fused to a benzene ring is benazepril.
There are also groups that are half ester and half amide. They are known as carbamates (or urethanes). Some examples of cyclic carbamates are rivaroxaban, metaxalone, zolmitriptan, furazolidone, linezolid etc.






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    Amide analogue of lactons are lactams, their tautomeric forms are lactims. Citing from the IUPAC Nomenclature of Organic Chemistry (Preferred names 2013):




    P-66.1.5.1 Lactams and lactims



    Intramolecular amides of amino carboxylic acids, $ce{-CO-NHbond{-}}$, are
    called ‘lactams’ and their tautomers, $ce{-C(OH)=Nbond{-}}$, are ‘lactims’. Lactams named in two ways:



      (1) as heterocyclic pseudoketones;



      (2) by substituting ‘lactam’ for the ‘ic acid’ ending of the systematic ‘oic acid’ name for the parent acid without the amino substituent, and inserting a locant designating the position of the amino group between the ‘o’ and the ‘lactam’. Method ‘lactams’. Lactims are named in the same way, using ‘lactim’ in place of ‘lactam’.



    (1) generates preferred IUPAC names.



    Examples:



    Fig.1



    pyrrolidin-2-one (PIN)

    butano-4-lactam



    (…)



    enter image description here



    3,4,5,6-tetrahydropyridin-2-ol (PIN)

    pentano-5-lactim




    (Note that the numberings depicted are for the preferred names (PINs) based on nitrogen heterocyclics)



    There's no (at least IUPAC) term for lactides analogue (‘lactide’ is not used in IUPAC names themselves anyway), but they exist.



    In traditional or general names, the Greek letter numbering is used, e.g. ε-caprolactam, or β-lactam four-membered ring part in bicyclic penicillin skeleton.






    share|improve this answer



















    • 2




      Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
      – Mathew Mahindaratne
      Nov 23 at 8:46






    • 1




      @MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
      – AbhigyanC
      Nov 23 at 11:21










    • @AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
      – Mithoron
      Nov 24 at 21:45















    up vote
    7
    down vote













    Amide analogue of lactons are lactams, their tautomeric forms are lactims. Citing from the IUPAC Nomenclature of Organic Chemistry (Preferred names 2013):




    P-66.1.5.1 Lactams and lactims



    Intramolecular amides of amino carboxylic acids, $ce{-CO-NHbond{-}}$, are
    called ‘lactams’ and their tautomers, $ce{-C(OH)=Nbond{-}}$, are ‘lactims’. Lactams named in two ways:



      (1) as heterocyclic pseudoketones;



      (2) by substituting ‘lactam’ for the ‘ic acid’ ending of the systematic ‘oic acid’ name for the parent acid without the amino substituent, and inserting a locant designating the position of the amino group between the ‘o’ and the ‘lactam’. Method ‘lactams’. Lactims are named in the same way, using ‘lactim’ in place of ‘lactam’.



    (1) generates preferred IUPAC names.



    Examples:



    Fig.1



    pyrrolidin-2-one (PIN)

    butano-4-lactam



    (…)



    enter image description here



    3,4,5,6-tetrahydropyridin-2-ol (PIN)

    pentano-5-lactim




    (Note that the numberings depicted are for the preferred names (PINs) based on nitrogen heterocyclics)



    There's no (at least IUPAC) term for lactides analogue (‘lactide’ is not used in IUPAC names themselves anyway), but they exist.



    In traditional or general names, the Greek letter numbering is used, e.g. ε-caprolactam, or β-lactam four-membered ring part in bicyclic penicillin skeleton.






    share|improve this answer



















    • 2




      Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
      – Mathew Mahindaratne
      Nov 23 at 8:46






    • 1




      @MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
      – AbhigyanC
      Nov 23 at 11:21










    • @AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
      – Mithoron
      Nov 24 at 21:45













    up vote
    7
    down vote










    up vote
    7
    down vote









    Amide analogue of lactons are lactams, their tautomeric forms are lactims. Citing from the IUPAC Nomenclature of Organic Chemistry (Preferred names 2013):




    P-66.1.5.1 Lactams and lactims



    Intramolecular amides of amino carboxylic acids, $ce{-CO-NHbond{-}}$, are
    called ‘lactams’ and their tautomers, $ce{-C(OH)=Nbond{-}}$, are ‘lactims’. Lactams named in two ways:



      (1) as heterocyclic pseudoketones;



      (2) by substituting ‘lactam’ for the ‘ic acid’ ending of the systematic ‘oic acid’ name for the parent acid without the amino substituent, and inserting a locant designating the position of the amino group between the ‘o’ and the ‘lactam’. Method ‘lactams’. Lactims are named in the same way, using ‘lactim’ in place of ‘lactam’.



    (1) generates preferred IUPAC names.



    Examples:



    Fig.1



    pyrrolidin-2-one (PIN)

    butano-4-lactam



    (…)



    enter image description here



    3,4,5,6-tetrahydropyridin-2-ol (PIN)

    pentano-5-lactim




    (Note that the numberings depicted are for the preferred names (PINs) based on nitrogen heterocyclics)



    There's no (at least IUPAC) term for lactides analogue (‘lactide’ is not used in IUPAC names themselves anyway), but they exist.



    In traditional or general names, the Greek letter numbering is used, e.g. ε-caprolactam, or β-lactam four-membered ring part in bicyclic penicillin skeleton.






    share|improve this answer














    Amide analogue of lactons are lactams, their tautomeric forms are lactims. Citing from the IUPAC Nomenclature of Organic Chemistry (Preferred names 2013):




    P-66.1.5.1 Lactams and lactims



    Intramolecular amides of amino carboxylic acids, $ce{-CO-NHbond{-}}$, are
    called ‘lactams’ and their tautomers, $ce{-C(OH)=Nbond{-}}$, are ‘lactims’. Lactams named in two ways:



      (1) as heterocyclic pseudoketones;



      (2) by substituting ‘lactam’ for the ‘ic acid’ ending of the systematic ‘oic acid’ name for the parent acid without the amino substituent, and inserting a locant designating the position of the amino group between the ‘o’ and the ‘lactam’. Method ‘lactams’. Lactims are named in the same way, using ‘lactim’ in place of ‘lactam’.



    (1) generates preferred IUPAC names.



    Examples:



    Fig.1



    pyrrolidin-2-one (PIN)

    butano-4-lactam



    (…)



    enter image description here



    3,4,5,6-tetrahydropyridin-2-ol (PIN)

    pentano-5-lactim




    (Note that the numberings depicted are for the preferred names (PINs) based on nitrogen heterocyclics)



    There's no (at least IUPAC) term for lactides analogue (‘lactide’ is not used in IUPAC names themselves anyway), but they exist.



    In traditional or general names, the Greek letter numbering is used, e.g. ε-caprolactam, or β-lactam four-membered ring part in bicyclic penicillin skeleton.







    share|improve this answer














    share|improve this answer



    share|improve this answer








    edited Nov 23 at 11:34

























    answered Nov 23 at 6:53









    mykhal

    3,81912054




    3,81912054








    • 2




      Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
      – Mathew Mahindaratne
      Nov 23 at 8:46






    • 1




      @MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
      – AbhigyanC
      Nov 23 at 11:21










    • @AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
      – Mithoron
      Nov 24 at 21:45














    • 2




      Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
      – Mathew Mahindaratne
      Nov 23 at 8:46






    • 1




      @MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
      – AbhigyanC
      Nov 23 at 11:21










    • @AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
      – Mithoron
      Nov 24 at 21:45








    2




    2




    Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
    – Mathew Mahindaratne
    Nov 23 at 8:46




    Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
    – Mathew Mahindaratne
    Nov 23 at 8:46




    1




    1




    @MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
    – AbhigyanC
    Nov 23 at 11:21




    @MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
    – AbhigyanC
    Nov 23 at 11:21












    @AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
    – Mithoron
    Nov 24 at 21:45




    @AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
    – Mithoron
    Nov 24 at 21:45










    up vote
    0
    down vote













    Cyclic amides are known as lactams. They can be a β-lactam which is a 4-membered ring, a γ-lactam which is a 5-membered ring, a δ-lactam which is a 6- membered ring, an ε-lactam which is 7-membered ring, and so on.
    An example of a drug containing a β-lactam ring is ezetimibe. Antibiotics that contain a β-lactam ring are collectively known as β-lactam antibiotics which include penicillins such as amoxicillin, cephalosporins such as cephalexin, cephamycins such as cefoxitin, carbacephems such as loracarbef, carbapenems such as doripenem, monobactams such as aztreonam, oxacephems such as moxalactam.
    Examples of drugs containing a γ-lactam ring include levetiracetam, doxapram, glimepiride.
    Examples of drugs containing a δ-lactam ring include perampanel, milrinone, pirfenidone.
    Example of a drug containing an ε-lactam ring fused to a benzene ring is benazepril.
    There are also groups that are half ester and half amide. They are known as carbamates (or urethanes). Some examples of cyclic carbamates are rivaroxaban, metaxalone, zolmitriptan, furazolidone, linezolid etc.






    share|improve this answer








    New contributor




    Isaac Lai is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
    Check out our Code of Conduct.






















      up vote
      0
      down vote













      Cyclic amides are known as lactams. They can be a β-lactam which is a 4-membered ring, a γ-lactam which is a 5-membered ring, a δ-lactam which is a 6- membered ring, an ε-lactam which is 7-membered ring, and so on.
      An example of a drug containing a β-lactam ring is ezetimibe. Antibiotics that contain a β-lactam ring are collectively known as β-lactam antibiotics which include penicillins such as amoxicillin, cephalosporins such as cephalexin, cephamycins such as cefoxitin, carbacephems such as loracarbef, carbapenems such as doripenem, monobactams such as aztreonam, oxacephems such as moxalactam.
      Examples of drugs containing a γ-lactam ring include levetiracetam, doxapram, glimepiride.
      Examples of drugs containing a δ-lactam ring include perampanel, milrinone, pirfenidone.
      Example of a drug containing an ε-lactam ring fused to a benzene ring is benazepril.
      There are also groups that are half ester and half amide. They are known as carbamates (or urethanes). Some examples of cyclic carbamates are rivaroxaban, metaxalone, zolmitriptan, furazolidone, linezolid etc.






      share|improve this answer








      New contributor




      Isaac Lai is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
      Check out our Code of Conduct.




















        up vote
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        down vote










        up vote
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        Cyclic amides are known as lactams. They can be a β-lactam which is a 4-membered ring, a γ-lactam which is a 5-membered ring, a δ-lactam which is a 6- membered ring, an ε-lactam which is 7-membered ring, and so on.
        An example of a drug containing a β-lactam ring is ezetimibe. Antibiotics that contain a β-lactam ring are collectively known as β-lactam antibiotics which include penicillins such as amoxicillin, cephalosporins such as cephalexin, cephamycins such as cefoxitin, carbacephems such as loracarbef, carbapenems such as doripenem, monobactams such as aztreonam, oxacephems such as moxalactam.
        Examples of drugs containing a γ-lactam ring include levetiracetam, doxapram, glimepiride.
        Examples of drugs containing a δ-lactam ring include perampanel, milrinone, pirfenidone.
        Example of a drug containing an ε-lactam ring fused to a benzene ring is benazepril.
        There are also groups that are half ester and half amide. They are known as carbamates (or urethanes). Some examples of cyclic carbamates are rivaroxaban, metaxalone, zolmitriptan, furazolidone, linezolid etc.






        share|improve this answer








        New contributor




        Isaac Lai is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
        Check out our Code of Conduct.









        Cyclic amides are known as lactams. They can be a β-lactam which is a 4-membered ring, a γ-lactam which is a 5-membered ring, a δ-lactam which is a 6- membered ring, an ε-lactam which is 7-membered ring, and so on.
        An example of a drug containing a β-lactam ring is ezetimibe. Antibiotics that contain a β-lactam ring are collectively known as β-lactam antibiotics which include penicillins such as amoxicillin, cephalosporins such as cephalexin, cephamycins such as cefoxitin, carbacephems such as loracarbef, carbapenems such as doripenem, monobactams such as aztreonam, oxacephems such as moxalactam.
        Examples of drugs containing a γ-lactam ring include levetiracetam, doxapram, glimepiride.
        Examples of drugs containing a δ-lactam ring include perampanel, milrinone, pirfenidone.
        Example of a drug containing an ε-lactam ring fused to a benzene ring is benazepril.
        There are also groups that are half ester and half amide. They are known as carbamates (or urethanes). Some examples of cyclic carbamates are rivaroxaban, metaxalone, zolmitriptan, furazolidone, linezolid etc.







        share|improve this answer








        New contributor




        Isaac Lai is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
        Check out our Code of Conduct.









        share|improve this answer



        share|improve this answer






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        answered 7 hours ago









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