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13.11.1.4.1.3.2 Method 2: By Carbon

DOI: 10.1055/sos-SD-013-00458

Koutentis, P. A.Science of Synthesis, (200413321.

3-Alkyl-4-aryl- and 3,4-diaryl-1,2,5-thiadiazoles can be prepared from 4-substituted 3-halo-1,2,5-thiadiazoles via a palladium-catalyzed cross-coupling reaction with arylstannanes in a reaction analogous to that shown in Section 13.11.1.4.1.4.1.[‌108‌] Treatment of 1,2,5-thiadiazoles with Grignard reagents usually results in ring opening,[‌109‌,‌110‌] however, the replacement of the chlorine atom of the thiadiazole 44 by alkyl groups derived from alkylmagnesium bromides, to give the thiadiazoles 45 (Scheme 29) appears more likely to occur via a direct displacement reaction.[‌46‌] When the substituent at the 3-position is propyl, pentyl, heptyl, or octyl, the product 45 is isolated as the oxalate salt.

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