Synthesis

Cycloaddition chemistry of anhydro-4-hydroxy-1, 3-thiazolium hydroxides (thioisomünchnones) for the synthesis of heterocycles

A Padwa, SR Harring, DL Hertzog, WR Nadler

Index: Padwa; Harring; Hertzog; Nadler Synthesis, 1994 , # 9 p. 993 - 1004

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Citation Number: 28

Abstract

bromoacetyl chloride and triethylamine in the presence of one equivalent of N- phenylmaleimide afforded cycloadducts 10 and 11 in 54% and 64% yield, respectively. These compounds are derived by dipolar cycloaddition of the mesoionic species 9 with the added dipolarophile. Cycloaddition of thioisomiinchnone 9 with an unsymmetrical dipolarophile such as phenyl vinyl sulfone afforded cycloadduct 12. The regiochemical ...