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27.9.1.1.5.1 Variation 1: By Condensation with Dimethylformamide Dimethyl Acetal

DOI: 10.1055/sos-SD-027-00330

Fišera, L.Science of Synthesis, (200427352.

The N-acyl-N,N-dimethyl amidines 13 are prepared in good yields (4191%) 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]

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References


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