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Paper | Regular issue | Vol 24, No. 12, 1986, pp.3433-3439
Published online, 1st January, 1970
DOI: 10.3987/R-1986-12-3433
Heterocyclic Rearrangements. Rearrangements of 1,2,4-Oxadiazoles, Isoxazoles, and 1,2,5-Oxadiazoles Involving a Carbethoxythiourea NCS Sequence

Gabriella Macaluso, Giuseppe Cusmano, Silvestre Buscemi, Vincenzo Frenna, Nicolò Vivona,* and Michele Ruccia

*Instituto de Chimica Organica, Facolta de Scienze, Università digli Studi di Palermo, 20 via Archirafi, 90123 Palermo, Italy

Abstract

The reaction of 3-amino-1,2,4-oxadiazoles 6a,b, 3-aminoisoxazole 9 and 3-amino-1,2,5-oxadiazoles 12a,b with ethoxycarbonyl isothiocyanate has been investigated. In the case of 6a,b, the reaction directly gave the 1,2,4-thiadiazoles 8a,b, because of a spontaneous rearrangement of the initially formed thioureas 7a,b. In the case of 9 and 12a,b, the reaction allowed to isolate the corresponding thioureas which were easily rearranged into 1,2,4-thiadiazoles.