Aromatic azapentalenes: 1 H-and (mesoionic) 2 H-pyrrolotetrazoles. Part 1. Synthesis and spectral characteristics 1

D Moderhack, D Decker, B Holtmann

Index: Moderhack; Decker; Holtmann Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 8 p. 720 - 728

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Citation Number: 5

Abstract

Two separate series of the title systems have been prepared by cyclisation of tetrazolium salts having acylmethyl functions attached to both the ring carbon and the adjacent nitrogen atom (3, 4):(i) working in an acetate buffer led to 7-acyl derivatives (5, 6; Scheme 3), and (ii) treatment with anhydride–base gave 5, 7-diacyl compounds by a deviating ring closure mechanism (11, 12; Scheme 4). These materials could be defunctionalised to afford ...