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SYNTHESIS OF SYMMETRICAL 1,6-DIHETERO-6aλ4-THIA-3,4-DIAZAPENTALENES FROM 5-AMINO-1,2,3,4-THIATRIAZOLE
Gerrit, L'abbe,Vermeulen, Guido
, p. 89 - 98 (2007/10/02)
1,6-Dioxa-6aλ4-thia-3,4-diazapentalenes 7 and 1,3,4,6-tetraaza-6aλ4-thiapentalenes 15, two new classes of compounds with single bond - no bond resonance, have been prepared by reaction of 5-amino-1,2,3,4-thiatriazole 4 with acyl chlorides and imidoyl chlorides.In the latter case, the salts of 5-imino-Δ3-1,2,4-thiadiazolines 12 were first isolated and subsequently reacted with a second equivalent of imidoyl chloride.This also led to the synthesis of unsimmetrically substituted 1,3,4,6-tetraaza-6aλ4-thiapentalenes.In the presence of bases, the salts 12 decompose via the isolable free bases 13 into N-cyanoamidines 14 and sulfur.Treatment of the dioxathiapentalenes 7 with P4S10, or direct thiobenzoylation of 4 gave the 3,4-diaza-1,6aλ4-trithiapentalenes 9.
