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7346

SOME REACTIONS OF N-(4-ACETYLPHENYL)-2-CYANOACETAMIDE WITH VARIOUS ELECTROPHILIC REAGENTS: SYNTHESIS OF THIAZOLIDINONES, 3,5-DICYANO-6-AMINO-2-OXOPYRIDINE, 2-IMINO-2H-CHROMENE-3-C

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Last updated: 03 Jan 2025

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Chemistry

Abstract

Reactions of N-(4-acetylphenyl)-2-cyanoacetamide (1) with several electrophilic reagents are reported. Thus, N-(4-acetylphenyl)-2-cyano-2-(3-phenylthiazol-2-ylidene)acetamide derivatives 4,5a-c were obtained. 4,6-dimethyl-2-oxo-1-(4-acetylphenyl)-1,2-dihydropyridine-3-carbonitrile (8) and their thiosemicarbazone derivative (9) were synthesized. Treatment of 1 and its thiosemicarbazone derivative 6 with α-cyanocinnamonitrile 10a,b under Michael reaction conditions afforded N-(4-acetylphenyl)-2-cyano-3-(4-methoxyphenyl)acrylamide (12) and 6-amino-4-(4-chlorophenyl)-3,5-dicyano-2-oxo-pyridine derivative 15, respectively. Condensation of 6 with α-halocarbonyl compounds gave 1,3-thiazole derivatives 16a,b & 17a,b which on treatment of 16a, 17a with salicyaldehyde gave 2-iminochromene derivatives 18 and 19, respectively. Treatment of 1 with phenolic aldehydes yielded 2-iminochromenes 21a,b which on treatment with ethanolic HCl gave chromene-2-one derivatives 22a,b, respectively. Treatment of 21a with malononitrile and/or ethyl cyanoacetate gave chromeno[3,4-c]pyridine derivatives 24 & 26. IR, 1HNMR and MS for the new synthesized compounds are cited.

DOI

10.21608/absb.2010.7346

Keywords

N-(4-ACETYLPHENYL)-2-CYANOACETAMIDE

Authors

First Name

MOHAMMED

Last Name

SALEM

MiddleName

A.

Affiliation

Chemistry Department, Faculty of Science, Alazhar University, 11284 Nasr City, Cairo, Egypt.

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Volume

21

Article Issue

Issue 1-A

Related Issue

1398

Issue Date

2010-06-01

Receive Date

2010-01-01

Publish Date

2010-06-01

Page Start

217

Page End

232

Print ISSN

1110-2535

Online ISSN

2636-3305

Article File

ABSB_Volume 21_Issue Issue 1-A_Pages 217-232.pdf

PDF . 197.6kB

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https://absb.journals.ekb.eg/article_7346.html

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https://absb.journals.ekb.eg/service?article_code=7346

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16

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Original Article

Type Code

520

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Journal

Publication Title

Al-Azhar Bulletin of Science

Publication Link

https://absb.journals.ekb.eg/

MainTitle

SOME REACTIONS OF N-(4-ACETYLPHENYL)-2-CYANOACETAMIDE WITH VARIOUS ELECTROPHILIC REAGENTS: SYNTHESIS OF THIAZOLIDINONES, 3,5-DICYANO-6-AMINO-2-OXOPYRIDINE, 2-IMINO-2H-CHROMENE-3-CARBOXAMIDE AND 5-IMINO-3H-CHROMENO[3,4-C]PYRIDINE-1-CARBONITRILE DERIVATIVES

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Article

Created At

22 Jan 2023