The Journal of Organic Chemistry

Synthesis of azocine derivatives from thio aldehyde Diels-Alder adducts

E Vedejs, JS Stults

Index: Vedejs, E.; Stults, J. S. Journal of Organic Chemistry, 1988 , vol. 53, # 10 p. 2226 - 2232

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Citation Number: 48

Abstract

Nitrogen-containing phenacyl sulfides 1 or 2 can be readily cleaved to thioaldehydes that are trapped by electron-rich dienes to give the adducts 4, 5, 11, or 17. The adducts have electrophilic character a to sulfur and can be converted into structures having new CN bonds at the a-carbon. Thus, 4 leads to lactam 6 by S to N acyl transfer. A similar reaction occurs from 15 to the eight-membered 16. Internal addition of amine nitrogen to Danishefsky ...

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