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Paper | Regular issue | Vol 91, No. 12, 2015, pp.2327-2342
Published online, 20th November, 2015
DOI: 10.3987/COM-15-13336
Novel Synthesis of 1,2-Dihydro-4H-3,1-benzoxazine-4-thiones by the Reaction of Newsynthesized Methyl Dithioanthranilate Hydrobromide with Carbonyl Compounds and the Formation of Another New Class of 1,2-Dihydro-4H-3,1-benzothiazine-4-thiones from the Same Reactants in the Presence of Excess Sodium Hydrogensulfide

Tatsuo Yamamoto* and Motomu Muraoka

*Faculty of Science, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan

Abstract

Methyl dithioanthranilate hydrobromide (6) was synthesized by the deprotection of Z-protected methyl dithioanthranilate (5) which was obtained by treatment of Z-protected methylthioiminium iodide 4 with H2S. The 1,2-dihydro-4H-3,1-benzoxazine-4-thiones 10a-m were first synthesized by the reaction of methyl dithioanthranilate hydrobromide (6) with each aldehyde or ketone. Formaldehyde, in this reaction, gave N-(methylthio)methyl-4H-3,1- benzoxazine-4-thione (11). Another new class of 1,2-dihydro-4H-3,1- benzothiazine-4-thiones 12a-e were synthesized from the same reactants in the presence of two equivalents of sodium hydrogensulfide.