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Valence isomerization of imidoyl isothiocyanates

✍ Scribed by Herbert M. Blatter; Halina Lukaszewski


Publisher
Elsevier Science
Year
1964
Tongue
French
Weight
267 KB
Volume
5
Category
Article
ISSN
0040-4039

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✦ Synopsis


We wish to report the prepsration and novel ring closure reaction of a new class of canpounds, the imldoyl isothlocyanates (I) (1). Imldoylisothlocyauates, prepared frcm lmidoylchlorides andmetalthlocyanates In solvents such as benzene, readily ring close to 4(5E)-qulnazoliuethiones (II) (2) often at temperatures as low as 80" (refluxing benzene). This ring closure, typified by the examples in Table I (J), represents a unique general synthesis of 4(3H)-qulnazollnethiones, and Is apparently the first such of this class of cmpounds to be Independent of the use of anthranili~ acid derivatives (5,6). It should be noted that closure occurs regardless of the presence of electron withdrawing substltuents such as l


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THIOCYANIC acid esters have long been known to undergo thermal isomerization to give the corresponding isothiocyanic acid esters. Although the isomerization reaction is believed to be quite general and is frequently used as a synthetic route to isothiocyanates, little is known about its nature and m