American Journal of Heterocyclic Chemistry

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Study on the Condensation of Different Hydroxy Aromatic Aldehydes with 2-Substituted 2-Oxazolin-5-ones Generated in situ

Received: 25 January 2019    Accepted: 14 March 2019    Published: 08 April 2019
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Abstract

In view to synthesize some bioactive 2-Substituted 4-(hydroxybenzylidene)-2-oxazolin-5-ones through a disciplined route, a study on the condensation of 2-, 3- and 4- hydroxy aromatic aldehydes (6) with 2-Substituted 2-oxazolin-5-ones (5) was carried out. 2-Substituted 2-oxazolin-5-ones (5) which are also known as saturated azlactones and unstable, were generated in situ from α-N-Acylglycines (1) using various cyclising agents namely ethyl chloroformate (2), benzene sulphonyl chloride (3) and p-toluene sulphonyl chloride (4) in dry benzene in presence of triethylamine base. The hydroxyl group at 3- and 4- positions of aromatic aldehydes namely 4-hydroxy-3-methoxybenzaldehyde (6a), m-hydroxybenzaldehyde (6b)and p-hydroxybenzaldehyde (6c) produce 2-substituted 4-(p-hydroxy-m-methoxybenzylidene)-2-oxazolin-5-one (8a), 2-substituted-4 (m-hydroxybenzylidene)-2-oxazolin-5-one (8b) and2-substituted-4 (p-hydroxybenzylidene)-2-oxazolin-5-one (8c) respectively as their (Z)-isomers, whereas 2-hydroxy aromatic aldehyde namely salicylaldehydeproduces 3-N-acylaminocoumarins (9) on condensation with 2-Substituted 2-oxazolin-5-ones (5) in appreciable yields and good purity. The reaction seems to be initiated by the formation of an adduct (E)-2-substituted 4-(o-hydroxybenzylidene-2-oxazolin-5-ones (7), followed by intramolecular 1,5- bond cleavage of the 2-oxazolin-5-one ring by the vicinal phenolic group and subsequent recyclization led to the formation of resultant 3-N-acylaminocoumarins (9). It is noteworthy that free hydroxyl group bearing benzylidene moiety at 4-position of 2-oxazolin-5-ones (8) were obtained. All the steps can be carried out in one flask.

DOI 10.11648/j.ajhc.20190501.11
Published in American Journal of Heterocyclic Chemistry (Volume 5, Issue 1, March 2019)
Page(s) 1-3
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This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

4-(Hydroxybenzylidene) Azlactones, 3-N-Acylaminocoumarins, Cyclisingagents, Synthons, in situ

References
[1] Sharma N, Banerjee J, Shrestha N and Choudhury D, A review on oxazolone, European J. Biomedical and Pharmaceutical Sciences 2015; 2: 964-87.
[2] Jat RL, Mishra R and Pathak D, International J. Pharmacy and Pharmaceutical Sciences 2012; 4: 378-80.
[3] Erlenmeyer E and Stadlin W, Liebigs. Ann. chem. 1904; 337: 283-85.
[4] Baltazzi E and Devis EA, Chem. Ind. (London) 1962; 929.
[5] Takagaki H, Tanabe S, Asoka M and Takel H, Chem. Lett.1979; 347-50.
[6] Tripathy PK, Indian J. Heterocyclic Chem.1992; 2: 77-80.
[7] Review: Rao YS and Filler R, Synthesis 1975; 749-64.
[8] Erlenmeyer E and Matter O, Liebigs. Ann. Chem. 1904; 337:271-3.
[9] Tripathy PK and Mukerjee AK, Indian J. Chem. 1987; 26B: 61-62.
[10] Ashare Ram and Mukerjee AK, Indian J. Chem. 1986; 25B: 423-24.
[11] Tripathy PK and Mukerjee AK, Heterocycles 1987; 26:1517-20.
[12] Mogilaiah K, Prashanthi M and Reddy CH, Indian J. Chem. 2003; 42B: 2126-28.
[13] Marrian DH, Russel PB and Todd AR, Biochem. J. 1949; 45: 533.
[14] Kirby GW, Michael J and Narayanaswami S, J. Chem. Soc. Perkin Trans- 1 1972; 203.
[15] Mukerjee AK and Ashare Ram, Chemical Reviews 1991; 91: 1-24.
Author Information
  • Department of Chemistry, North Eastern Regional Institute of Science and Technology, Nirjuli, Itanagar, India

  • Department of Chemistry, North Eastern Regional Institute of Science and Technology, Nirjuli, Itanagar, India

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    Pubanita Bhuyan, Pradeep K. Tripathy. (2019). Study on the Condensation of Different Hydroxy Aromatic Aldehydes with 2-Substituted 2-Oxazolin-5-ones Generated in situ. American Journal of Heterocyclic Chemistry, 5(1), 1-3. https://doi.org/10.11648/j.ajhc.20190501.11

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    Pubanita Bhuyan; Pradeep K. Tripathy. Study on the Condensation of Different Hydroxy Aromatic Aldehydes with 2-Substituted 2-Oxazolin-5-ones Generated in situ. Am. J. Heterocycl. Chem. 2019, 5(1), 1-3. doi: 10.11648/j.ajhc.20190501.11

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    Pubanita Bhuyan, Pradeep K. Tripathy. Study on the Condensation of Different Hydroxy Aromatic Aldehydes with 2-Substituted 2-Oxazolin-5-ones Generated in situ. Am J Heterocycl Chem. 2019;5(1):1-3. doi: 10.11648/j.ajhc.20190501.11

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  • @article{10.11648/j.ajhc.20190501.11,
      author = {Pubanita Bhuyan and Pradeep K. Tripathy},
      title = {Study on the Condensation of Different Hydroxy Aromatic Aldehydes with 2-Substituted 2-Oxazolin-5-ones Generated in situ},
      journal = {American Journal of Heterocyclic Chemistry},
      volume = {5},
      number = {1},
      pages = {1-3},
      doi = {10.11648/j.ajhc.20190501.11},
      url = {https://doi.org/10.11648/j.ajhc.20190501.11},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.ajhc.20190501.11},
      abstract = {In view to synthesize some bioactive 2-Substituted 4-(hydroxybenzylidene)-2-oxazolin-5-ones through a disciplined route, a study on the condensation of 2-, 3- and 4- hydroxy aromatic aldehydes (6) with 2-Substituted 2-oxazolin-5-ones (5) was carried out. 2-Substituted 2-oxazolin-5-ones (5) which are also known as saturated azlactones and unstable, were generated in situ from α-N-Acylglycines (1) using various cyclising agents namely ethyl chloroformate (2), benzene sulphonyl chloride (3) and p-toluene sulphonyl chloride (4) in dry benzene in presence of triethylamine base. The hydroxyl group at 3- and 4- positions of aromatic aldehydes namely 4-hydroxy-3-methoxybenzaldehyde (6a), m-hydroxybenzaldehyde (6b)and p-hydroxybenzaldehyde (6c) produce 2-substituted 4-(p-hydroxy-m-methoxybenzylidene)-2-oxazolin-5-one (8a), 2-substituted-4 (m-hydroxybenzylidene)-2-oxazolin-5-one (8b) and2-substituted-4 (p-hydroxybenzylidene)-2-oxazolin-5-one (8c) respectively as their (Z)-isomers, whereas 2-hydroxy aromatic aldehyde namely salicylaldehydeproduces 3-N-acylaminocoumarins (9) on condensation with 2-Substituted 2-oxazolin-5-ones (5) in appreciable yields and good purity. The reaction seems to be initiated by the formation of an adduct (E)-2-substituted 4-(o-hydroxybenzylidene-2-oxazolin-5-ones (7), followed by intramolecular 1,5- bond cleavage of the 2-oxazolin-5-one ring by the vicinal phenolic group and subsequent recyclization led to the formation of resultant 3-N-acylaminocoumarins (9). It is noteworthy that free hydroxyl group bearing benzylidene moiety at 4-position of 2-oxazolin-5-ones (8) were obtained. All the steps can be carried out in one flask.},
     year = {2019}
    }
    

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    AU  - Pubanita Bhuyan
    AU  - Pradeep K. Tripathy
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    DO  - 10.11648/j.ajhc.20190501.11
    T2  - American Journal of Heterocyclic Chemistry
    JF  - American Journal of Heterocyclic Chemistry
    JO  - American Journal of Heterocyclic Chemistry
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    PB  - Science Publishing Group
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    UR  - https://doi.org/10.11648/j.ajhc.20190501.11
    AB  - In view to synthesize some bioactive 2-Substituted 4-(hydroxybenzylidene)-2-oxazolin-5-ones through a disciplined route, a study on the condensation of 2-, 3- and 4- hydroxy aromatic aldehydes (6) with 2-Substituted 2-oxazolin-5-ones (5) was carried out. 2-Substituted 2-oxazolin-5-ones (5) which are also known as saturated azlactones and unstable, were generated in situ from α-N-Acylglycines (1) using various cyclising agents namely ethyl chloroformate (2), benzene sulphonyl chloride (3) and p-toluene sulphonyl chloride (4) in dry benzene in presence of triethylamine base. The hydroxyl group at 3- and 4- positions of aromatic aldehydes namely 4-hydroxy-3-methoxybenzaldehyde (6a), m-hydroxybenzaldehyde (6b)and p-hydroxybenzaldehyde (6c) produce 2-substituted 4-(p-hydroxy-m-methoxybenzylidene)-2-oxazolin-5-one (8a), 2-substituted-4 (m-hydroxybenzylidene)-2-oxazolin-5-one (8b) and2-substituted-4 (p-hydroxybenzylidene)-2-oxazolin-5-one (8c) respectively as their (Z)-isomers, whereas 2-hydroxy aromatic aldehyde namely salicylaldehydeproduces 3-N-acylaminocoumarins (9) on condensation with 2-Substituted 2-oxazolin-5-ones (5) in appreciable yields and good purity. The reaction seems to be initiated by the formation of an adduct (E)-2-substituted 4-(o-hydroxybenzylidene-2-oxazolin-5-ones (7), followed by intramolecular 1,5- bond cleavage of the 2-oxazolin-5-one ring by the vicinal phenolic group and subsequent recyclization led to the formation of resultant 3-N-acylaminocoumarins (9). It is noteworthy that free hydroxyl group bearing benzylidene moiety at 4-position of 2-oxazolin-5-ones (8) were obtained. All the steps can be carried out in one flask.
    VL  - 5
    IS  - 1
    ER  - 

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