Treatment of N-substituted 2-(methylamino)naphthoquinones 3 and -anthracene-1,4-diones 4 with S2Cl2 and DABCO in chlorobenzene gave the corresponding 2,3-dihydronaphtho[2,3-d][1,3] thiazole-4,9-diones 1 and 2,3-dihydroanthra[2,3-d][1,3] thiazole-4,11-diones 2 by triethylamine addition, in high to moderate yields. The DABCO replacement for N-ethyldiisopropylamine in the reaction of anthracene-1,4-diones 4 led unexpectedly to the corresponding 2-thioxo-2,3-dihydroanthra[2,3-d][1,3] thiazole-4,11-diones 10. The reaction of 3H-spiro[1,3-thiazole-2,1'-cyclohexanes] 1d, 2d with Et3N in chlorobenzene under reflux yielded 2,3,4,5-tetrahydro-1H-carbazole-6,11-diones 15, 16, i.e., ring contraction and fusion products. A plausible mechanism was proposed for the formation of the products.

A one-pot and effective procedure has been developed for the synthesis of symmetrical diarylsulfur diimides from anilines, sulfur monochloride, and DABCO in good yields (70-90%). A plausible mechanism for this transformation has been proposed.

AbstractThe proposed intermediate (III) can be isolated at lower temperature and independently converted to sulfur diimides under similar conditions.

A new method for the synthesis of title benzoisothiazole (II) and its transformation into isothiazolopyrroloisoindole (V), a representative of a previously unknown heterocyclic system, are given.

1,3-Dipolar cycloaddition of 4,6-dinitrobenzo[c]isothiazole to (N-methyl-N-methylideneammonio)methanide (2 equiv.) gives 5,8-dimethyl-3b,6b-dinitrodecahydroisothiazolo[3,4-e]pyrrolo[3,4-g]isoindole, whose structure was confirmed by X-ray diffraction analysis.

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Treatment of N-substituted 2-methyl-1H-indoles 1 with S2Cl2 and DABCO in chloroform gave the corresponding [1,2]dithiolo[4,3-b]indole-3(4H)-thiones 5 by the addition of triethylamine in high yield. 1,2-Dithiole-3-thiones 5 underwent cycloaddition with one or two DMAD equivalents to afford either 2-(3-thioxo-1,3-dihydro-2H-indol-2-ylidene)-1,3-dithioles 10 or fused 4,5-dihydrothiopyrano[3,2-b]indoles 9.

Reaction of 4-isopropylamino-5-chloro-1,2-dithiole-3-ones 3 and S2Cl2 in acetonitrile gave selectively 3-oxo-bis[1,2]dithiolo[1,4]thiazine-5-thiones 1 by the addition of triethylamine and bis[1,2]dithiolo[1,4]thiazine-3,5-diones 5 under the action of formic acid. 3,5-Diones 5 were also obtained by intramolecular cyclization of N,N-bis(5-chloro-3-oxo[1,2]dithiol-4-yl)amines 6 with S2Cl2 in the presence of Et3N.

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