%0 Journal Article
%T Synthesis of 2,3-dihydronaphtho[2,3-d][1,3]thiazole-4,9-diones and 2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-diones and novel ring contraction and fusion reaction of 3H-spiro[1,3-thiazole-2,1'-cyclohexanes] into 2,3,4,5-tetrahydro-1H-carbazole-6,11-diones
%A Lidia S. Konstantinova
%A Kirill A. Lysov
%A Ljudmila I. Souvorova
%A Oleg A. Rakitin
%J Beilstein Journal of Organic Chemistry
%D 2013
%I 
%R 10.3762/bjoc.9.62
%X 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.
%K anthracene-1
%K 4-diones
%K 1H-carbazole-6
%K 11-diones
%K fused thiazoles
%K fusion reaction
%K heterocycles
%K naphthoquinones
%K ring contraction
%K sulfur¨Cnitrogen
%U http://dx.doi.org/10.3762/bjoc.9.62