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Paper | Regular issue | Vol 68, No. 6, 2006, pp.1109-1119
Published online, 2nd May, 2006
DOI: 10.3987/COM-05-10644
Synthetic Utilization of Polynitroaromatic Compounds. 4. Synthesis of Nitro-free 4,6-Disubstituted-3-aminobenzothiophene Derivatives Based on 2,4,6-Trinitrobenzamide

Sergei G. Zlotin,* Pavel G. Kislitsin, Fedor A. Kucherov, and Andrei A. Gakh*

*Oak Ridge National Laboratory, Oak Ridge, TN 37831-6242, USA

Abstract

A convenient synthesis of nitro-free 4,6-disubstituted 3 aminobenzothiophenes, their S-oxides and S,S-dioxides based on the available 2,4,6-trinitrobenzamide has been developed. The synthesis entails stepwise nucleophilic substitution of all nitro groups in the starting compound by S-, N-, and O-nucleophiles followed by Thorpe-Ziegler cyclization.