Tetrahedron

Conformational analysis of substituted hexahydropyrrolo [2, 3-b] indoles and related systems. An unusual example of hindered rotation about sulfonamide S N …

D Crich, M Bruncko, S Natarajan, BK Teo, DA Tocher

Index: Crich; Bruncko; Natarajan; Teo; Tocher Tetrahedron, 1995 , vol. 51, # 8 p. 2215 - 2228

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Citation Number: 23

Abstract

An indepth comparison of the solution (CDCl3, 1H-NMR) and solid state (X-ray) conformations of the hexahydropyrrolo [2, 3-b] indoles 4, 5, and 6 is made. Close parallels with the literature conformations of the aflatoxin furo [2, 3-b] benzofuran skeleton and with the conformation of the naturally occuring hexahydropyrrolindole physostigmine are noted. In the solid state the sulfonamide N in 4–6 is non-planar with various degrees of rotation ...