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

Pubanita Bhuyan; Pradeep K. Tripathy

doi:doi:10.11648/j.ajhc.20190501.11

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

Pubanita Bhuyan, Pradeep K. Tripathy

Published in American Journal of Heterocyclic Chemistry (Volume 5, Issue 1)

Received: 25 January 2019 Accepted: 14 March 2019 Published: 8 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.

Published in	American Journal of Heterocyclic Chemistry (Volume 5, Issue 1)
DOI	10.11648/j.ajhc.20190501.11
Page(s)	1-3
Creative Commons	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), 2019. 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.

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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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ACS Style

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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AMA Style

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://article.sciencepublishinggroup.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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TY  - JOUR
T1  - Study on the Condensation of Different Hydroxy Aromatic Aldehydes with 2-Substituted 2-Oxazolin-5-ones Generated in situ
AU  - Pubanita Bhuyan
AU  - Pradeep K. Tripathy
Y1  - 2019/04/08
PY  - 2019
N1  - https://doi.org/10.11648/j.ajhc.20190501.11
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
SP  - 1
EP  - 3
PB  - Science Publishing Group
SN  - 2575-5722
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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Author Information

Pubanita Bhuyan

Department of Chemistry, North Eastern Regional Institute of Science and Technology, Nirjuli, Itanagar, India
Pradeep K. Tripathy

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

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APA Style

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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ACS Style

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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AMA Style

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://article.sciencepublishinggroup.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}
}

Copy | Download

TY  - JOUR
T1  - Study on the Condensation of Different Hydroxy Aromatic Aldehydes with 2-Substituted 2-Oxazolin-5-ones Generated in situ
AU  - Pubanita Bhuyan
AU  - Pradeep K. Tripathy
Y1  - 2019/04/08
PY  - 2019
N1  - https://doi.org/10.11648/j.ajhc.20190501.11
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
SP  - 1
EP  - 3
PB  - Science Publishing Group
SN  - 2575-5722
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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