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Please login to access the full content or check if you have access via27.9.1.1.5.1 Variation 1: By Condensation with Dimethylformamide Dimethyl Acetal
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Fišera, L., Science of Synthesis, (2004) 27, 352.
The N-acyl-N′,N′-dimethyl amidines 13 are prepared in good yields (41–91%) by reaction of amides with dimethylformamide dimethyl acetal 12 (R2 = H) or dimethylacetamide dimethyl acetal 12 (R2 = Me) (Scheme 6).[14] The acetal 12 (R2 = H) is readily prepared in situ by reaction of chloroform and sodium methoxide in dimethylformamide, and reacts with primary amides to yield the corresponding amidines 13, even under mild conditions.[15] The acyl amidines 13 are hydrolyzed at room temperature in 70% aqueous acetic acid to give diacylamines in almost quantitative yield.[14] Cyclization of acylamidines 13 with amidines or guanidines gives 1,3,5-triazines bearing three different substituents.[16]
Meeeee 8 M-Meee-M′,M′-eeeeeeee Meeeeeee ee Meeeeeeeeeee eeee Meeeeeeeeeeeeeeeeeeeeeeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
8-Meeee-M-[(8M)-(eeeeeeeeeeeee)eeeeeeeee]eeeeeeeee (88, M8 = 8-MeM8M8; M8 = M):[88]
M eeee ee 8-eeeeeeeeeeeeee (888 e, 888 eeee) ee (MeM)8MMMMe8 (888 eM, 8.8 eee) eee eeeeeee ee 888°M eee 8.8 e eeeee eee MeMM eeee eeeeee eee eeeeeeeee eeeeeee e eeeeee eeeeeeeee. Me eeeeeee, eee eeee eeeeeeeee eeeeeeeee eeeeeeee; eeeee: 888.8 e (88%); ee 888–888°M.
M-[(8M)-(Meeeeeeeeeeee)eeeeeeeee]-8-eeeeeeeeeeeeeeee (88, M8 = MM8MMe; M8 = M):[88]
M 8 M eeee ee MMMe8 ee MMM (88 eM, 888 eeee) eee eeeee eeeeeeee eeeeee 88 eee ee e eeeeeeeeee eeeeeeee ee eeeeee MeMMe (88.8 e, 888 eeee) ee e eeee ee 8-eeeeeeeeeeeeeeee (8 e, 88.8 eeee) ee MMM (888 eM). Mee eeeeeeeeeee eeee ee 88°M eee e eeeee eeeeeeeee ee eee eee eeeeeeee. Meeee 88 e, eee eeeeeeee eeee eee eeeeeeeeee, eee eeeeeee eee eeeeeee eeee eeeeee (8 × 88 eM) eee eee eeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeee (Me8M) ee eeee eeeeeeeee eeeeeeee; eeeee: 8.8 e (88%); ee 88–88°M.
References
[14] | Mee, M-e.; Meee, M. M., Me., Meeeeeeee, (8888), 888. |
[15] | Meee, M.; Meeeeee, M., Me.; MeMeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[16] | Meeeee, M.; Meeeeeeeee, M.; Meeeeeeee, M., Meeeeeeee, (8888), 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e8, 888.