Synthesis of 2-pyridinylbenzoxazole: mechanism for the intramolecular photosubstitution of the haloarene with the carbonyl oxygen of the amide bond in basic …

YT Park, CH Jung, KW Kim, HS Kim

Index: Park, Yong-Tae; Jung, Chang-Hee; Kim, Kwang-Wook; Kim, Ho Sik Journal of Organic Chemistry, 1999 , vol. 64, # 23 p. 8546 - 8556

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Citation Number: 30

Abstract

2-Pyridinylbenzoxazole derivatives have been synthesized by the intramolecular photosubstitution reaction of N-(2-halophenyl) pyridinecarboxamide (1 and 2) with its amide bond in basic medium. In neutral medium both intramolecular photosubstitution and photoreduction reactions occurred. In the photosubstitution reaction a singlet state of the o- haloarene is involved, whereas in the photoreduction a triplet state of the o-haloarene is ...