You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via13.11.1.4.1.3.2 Method 2: By Carbon
Please login to access the full content or check if you have access via
Koutentis, P. A., Science of Synthesis, (2004) 13, 321.
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.
Meeeee 88 Meeeeeee ee 8-Meeeeeeeeee 8-Meee-8,8,8-eeeeeeeeeeee eeee Meeeeeeeeeeeee Meeeeeee[88]
Meeeeeeeeeee Meeeeeeee
8-Meeeee-8-(8-eeeeee-8,8,8-eeeeeeeeee-8-ee)-8,8,8,8-eeeeeeeeeeeeeeeeee (88, M8 = Me); Meeeeee Meeeeeeee:[88]
Me e eeeeeee eeee ee 8-(8-eeeeee-8,8,8-eeeeeeeeee-8-ee)-8-eeeeee-8,8,8,8-eeeeeeeeeeeeeeeeee (88) (888 ee, 8.8 eeee) ee MMM (88 eM) ee 8°M eee eeeee eeeeeeee e eeee ee MeMeMe (8 eM, 8.8 eeee). Meeee 88 eee, eee eeeeeee eee eeeeeeee eeee M8M (88 eM) eee eeeeeeeee eeee Me8M (8 × 888 eM). Mee eeeeeeee eeee eeeee, eeeeeeeeee, eee eee eeeeeee eee eeeeeeeeeeee ee eee eeeeeee eeee ee 88 (M8 = Me); eeeee: 888 ee (88%); ee 888–888°M (eeeeeee).
References
[46] | Meeeeeeee, M.; Meeeee, M. M.; Meeeeee, M.; Meeeeeeeeee, M.; Meeeeeeee, M. M.; Meeeeé, M.; Meeee, M. M.; Meee, M. M.; Meee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[108] | Meeeeeee, M., Meeeeeeeeeee, (8888) 88, 8888. |
[109] | Meeeeee, M.; Me Meeee, M.; Meeeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
[110] | Meeeeee, M.; Meeeeeeeee, M.; Me Meeee, M., Meeeeeeee, (8888), 888. |