ChemInform Abstract: Stereochemical Studies. Part 86. Saturated Heterocycles. Part 81.

Abstract

Durch Reaktion der Aminosäuren (I), (II), (VI) und (VII) mit den Isothiocyanaten (V) entstehen die Tricyclen (III), (IV), (VIII) und (IX).

Isothiocyanates in the chemistry of heterocycles

“…Thus, the condensation of anthranilic acids with isothiocyanates gave 2-thio-4quinazolones,1,73,74 as shown in the conversion of 47 into 48 (eq 16).58 -H 48: R1 = H, R2 = MeCOCH2CH2 (78%) Methylene-bridged thioquinazolones 49 were obtained by similar approach and these were converted into new thiouracils 50 via retrodiene decomposition. 75,76 It is noteworthy that the reaction of allyl and aryl isothiocyanates with dimethylsulfoxonium [2-(methylamino) benzoyl] methylide furnished the corresponding thioquinazolones.77 Also, the condensation of isatoic anhydride with aryl isothiocyanates gave 3-aryl-2thio-4-quinazolones, apparently by cycloaddition of an intermediary iminoketene. 78 Heterocycles carrying an amino function with a vicinal carbonyl group were exploited for the construction of fused thiopyrimidine rings.…”