Photoreaction of 2′-chloro-4-R-benzanilide: Synthesis of 2-(4-R-phenyl)-1,3-benzoxazole and 9-R-phenanthridin-6(5H)-one (R=H, CH3, CH3O)

Ahmed M. Mayouf; Yong Tae Park

doi:10.1016/S1010-6030(02)00097-7

Photoreaction of 2′-chloro-4-R-benzanilide: Synthesis of 2-(4-R-phenyl)-1,3-benzoxazole and 9-R-phenanthridin-6(5H)-one (R=H, CH₃, CH₃O)

Ahmed M. Mayouf, Yong Tae Park

Research output: Journal Publication › Article › peer-review

12 Citations (Scopus)

Abstract

The UV photolysis of2′-chloro-4-R-benzanilides in acetonitrile solution under nitrogen atmosphere leads to the formation of intramolecular photocyclization products (9-R-phenanthridin-6(5)-one, 20-30%), along with the minor photoreduction, photo-Fries, and intramolecular photosubstitution products. The photoreaction of 2′-chloro-4-R-benzanilide in acetonitrile solution containing 10% of water or aqueous sodium hydroxide however gives 2-(4-R-phenyl)-1,3-benzoxazole as a major product (∼30%) along with the photoreduction, photo-Fries and intramolecular photocyclization products.

Original language	English
Pages (from-to)	115-123
Number of pages	9
Journal	Journal of Photochemistry and Photobiology A: Chemistry
Volume	150
Issue number	1-3
DOIs	https://doi.org/10.1016/S1010-6030(02)00097-7
Publication status	Published - 26 Jul 2002
Externally published	Yes

Keywords

2′-chloro-4-R-benzanilides
Intramolecular photocyclization
Intramolecular photosubstitution
Solvent and substituent effect

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
General Physics and Astronomy

Access to Document

10.1016/S1010-6030(02)00097-7

Cite this

@article{142b9e6a446d4252b3c53947e64c5a2f,

title = "Photoreaction of 2′-chloro-4-R-benzanilide: Synthesis of 2-(4-R-phenyl)-1,3-benzoxazole and 9-R-phenanthridin-6(5H)-one (R=H, CH3, CH3O)",

abstract = "The UV photolysis of2′-chloro-4-R-benzanilides in acetonitrile solution under nitrogen atmosphere leads to the formation of intramolecular photocyclization products (9-R-phenanthridin-6(5)-one, 20-30%), along with the minor photoreduction, photo-Fries, and intramolecular photosubstitution products. The photoreaction of 2′-chloro-4-R-benzanilide in acetonitrile solution containing 10% of water or aqueous sodium hydroxide however gives 2-(4-R-phenyl)-1,3-benzoxazole as a major product (∼30%) along with the photoreduction, photo-Fries and intramolecular photocyclization products.",

keywords = "2′-chloro-4-R-benzanilides, Intramolecular photocyclization, Intramolecular photosubstitution, Solvent and substituent effect",

author = "Mayouf, {Ahmed M.} and Park, {Yong Tae}",

year = "2002",

month = jul,

day = "26",

doi = "10.1016/S1010-6030(02)00097-7",

language = "English",

volume = "150",

pages = "115--123",

journal = "Journal of Photochemistry and Photobiology A: Chemistry",

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publisher = "Elsevier B.V.",

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T1 - Photoreaction of 2′-chloro-4-R-benzanilide

T2 - Synthesis of 2-(4-R-phenyl)-1,3-benzoxazole and 9-R-phenanthridin-6(5H)-one (R=H, CH3, CH3O)

AU - Mayouf, Ahmed M.

AU - Park, Yong Tae

PY - 2002/7/26

Y1 - 2002/7/26

N2 - The UV photolysis of2′-chloro-4-R-benzanilides in acetonitrile solution under nitrogen atmosphere leads to the formation of intramolecular photocyclization products (9-R-phenanthridin-6(5)-one, 20-30%), along with the minor photoreduction, photo-Fries, and intramolecular photosubstitution products. The photoreaction of 2′-chloro-4-R-benzanilide in acetonitrile solution containing 10% of water or aqueous sodium hydroxide however gives 2-(4-R-phenyl)-1,3-benzoxazole as a major product (∼30%) along with the photoreduction, photo-Fries and intramolecular photocyclization products.

AB - The UV photolysis of2′-chloro-4-R-benzanilides in acetonitrile solution under nitrogen atmosphere leads to the formation of intramolecular photocyclization products (9-R-phenanthridin-6(5)-one, 20-30%), along with the minor photoreduction, photo-Fries, and intramolecular photosubstitution products. The photoreaction of 2′-chloro-4-R-benzanilide in acetonitrile solution containing 10% of water or aqueous sodium hydroxide however gives 2-(4-R-phenyl)-1,3-benzoxazole as a major product (∼30%) along with the photoreduction, photo-Fries and intramolecular photocyclization products.

KW - 2′-chloro-4-R-benzanilides

KW - Intramolecular photocyclization

KW - Intramolecular photosubstitution

KW - Solvent and substituent effect

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