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DOI: 10.1055/sos-SD-210-00013

Chebanov, V. A.; Gorobets, N. Yu.; Sedash, Yu. V.Science of Synthesis: Multicomponent Reactions, (2014141.

Organosilicon compounds are widely used as water scavengers in reactions of carbonyl compounds.[‌77‌] In 1992, Zavʼyalov and Kulikova suggested using chlorotrimethylsilane in dimethylformamide as promoter of the Biginelli reaction. The desired 3,4-dihydropyrimidin-2(1H)-one derivatives are obtained in 62–80% yields from aromatic aldehydes and in 32–37% from aliphatic aldehydes at room temperature. The procedure includes two steps: first, the β-dicarbonyl compound and the aldehyde undergo aldol condensation to give an α,β-unsaturated ketone, and then urea is introduced into the reaction mixture to react with the product of the previous step. The final products are isolated and purified by chromatography.[‌78‌] Application of chlorotrimethylsilane was further developed for the synthesis of 2-(thi)oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (e.g., 13) of different types.[‌77‌,‌79‌] The advantage of the method is the possibility of using mono- and disubstituted ureas (Scheme 11).

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Meeeeeeeeee 88

M8 M8 M8 M Meeee (%) Mee
8-M8MM8M8 Me M M 88 [‌88‌]
Me Me M M 88 [‌88‌]
8-MeMM8M8 Me Me M 88 [‌88‌]

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Meeeeeeeeee 88

M8 M8 M8 M Meeee (%) Mee
Me Me Me M 88 [‌88‌]
8-MeMM8M8 Me Me M 88 [‌88‌]
8-Me8MM8M8 Me Me M 88 [‌88‌]
8,8-(MeM)8M8M8 Me Me M 88 [‌88‌]
8-MMM8M8 Me Me M 88 [‌88‌]
8-eeeee e-Me Me M 88 [‌88‌]
eMe Me Me M 88 [‌88‌]
MMMMMe Me Me M 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeee eee 8,8-Meeeeeeeeeeee Meeee 8-Meeeee-8-(eee)eee-8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

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Meeee 8-(8-Meeeeeeeeeeee)-8-eeeeee-8-eee-8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeeeeeeeeee (88, M8 = 8-MeMM8M8; M8 = Me; M8 = Me; M = M); Meeeeee Meeeeeeee:[‌88‌]

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