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Cyclic and Linear Adducts from Carbonic Ester Isothiocyanates and Imines of Different Type
Goerdeler, Joachim,Ho, Chuen-huei
, p. 1297 - 1308 (2007/10/02)
Various imines reacted with the isothiocyanates 4 to give 1:1-adducts (1,3-thiazetidines 1 and 3, dihydro-2H-1,3-thiazines 5, respectively) or to 2:1-adducts (tetrahydro-2H-1,3,5-thiadiazines 2), depending mainly on steric effects.In special cases linear adducts (thioureas 6 and vinylogous thioureas 7) were obtained, which in part formed 4-thiouracil 8. - Analytical data for the sequence RX-CO-N=C(NR-)-S- are presented. - Anomalous NMR spectra of the N-xylyl- and -mesityl derivatives of 1 presumably result from hindered rotation. - Benzyl azide and the isothiocyanates 4 afforded derivatives of 1,2,4-dithiazole 10 with elimination of nitro gen.
