Intramolecular capture of pummerer rearrangement intermediates. I. Synthesis of pyrrolo [2, 1??c][1, 4] benzothiazines

DK Bates, RT Winters, BA Sell

Index: Bates, Dallas K.; Winters, R. Thomas; Burnell, A. Sell Journal of Heterocyclic Chemistry, 1986 , vol. 23, # 3 p. 695 - 699

Full Text: HTML

Citation Number: 11

Abstract

Abstract Treatment of 1-(2-alkylsulfinylphenyl) pyrroles with trifluoroacetic acid in refluxing toluene gives 4-substituted pyrrolo [2, 1-c][1, 4] benzothiazines in good yield when the alkyl group bears an electron withdrawing substituent on the α-carbon. In the absence of such a group, starting material is recovered. The sulfoxides are prepared by oxidation (mCBPA) of the corresponding sulfide. The sulfides are prepared from 2-aminobenzenethiol either by ...