Science of Synthesis

Chebanov, V. A.; Gorobets, N. Yu.; Sedash, Yu. V., Science of Synthesis: Multicomponent Reactions, (2014) 1, 29.

General Introduction

The three-component Biginelli[‌1‌] condensation is today one of the most studied multicomponent reactions and is widely used for the construction of diverse molecules containing 3,4-dihydropyrimidin-2(1H)-one and 3,4-dihydropyrimidine-2(1H)-thione heterocycles [DHPMs; alternative names: 3,4-dihydro-2(1H)-pyrimidin(ethi)ones, 2-(thi)oxo-1,2,3,4-tetrahydropyrimidines]. To date there are more than 1000 publications on the Biginelli reaction and the number of reviews concerning this multicomponent reaction is approaching 100. Such high research interest is explained by the simple methodology and efficiency of this multicomponent reaction for diversity-oriented and focused synthesis. Furthermore, this reaction and its products are often used as models for testing novel catalytic systems,[‌2‌,‌3‌] process-intensification techniques,[‌4‌–‌9‌] methods for separation of enantiomers,[‌10‌,‌11‌] and other newly introduced chemical technologies.[‌12‌,‌13‌]

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Meeeeeeeeeee, eeeeeee 8,8-eeeeeeeeeeeeeeee-8(8M)-eee eeeeeeeeeee eeee eeee eeeeeeee ee eeeeeeeeeeeeeeee eee eeee-MMM eeeeee,[‌88‌,‌88‌] eeeeeeeeeeeeee, eeeeeeeeeeeee, eee eeeeeeeeeeeeeeeeee; eeee ee eeee eeee eeeeeee eeeeeeeeeeeeee, eeeeeeeeeeeee, eeeeeeeeeee,[‌88‌] eee eeeeeeeeeeeee eeeee eeeeeeeeee. Mee eee eeeeeee eeeee ee eee eeeeeeeeeeeeeee eeeeee ee Meeeeeeee eeeeeeee, eeeeee eeeee ee e eeeeee eeeeeeeeee eeeeee ee Meeeee eee Meeeee.[‌8‌]

‌Meeeee 8‌ Meeeeeeeee eee Meeeeeee Meeeeeee ee Meeeeeeee 8,8-Meeeeeeeeeeeeeee-8(8M)-eeee eee 8,8-Meeeeeeeeeeeeeeee-8(8M)-eeeeeee[‌8‌,‌88‌,‌88‌,‌88‌]

Me e eeeeeee eeeeeee ee e Meeeeeeee eeeeeeee, eee eee-eee, eeeee-eeeeeeeee eeeeeeeeeeee ee eeeeeeeeeeee, eeeee eeeeeeeeeeee, eee eeee ee eeeeeeeee eeeeeee eeeeeeee 8,8-eeeeeeeeeeeeeeee-8(8M)-eee ‌8‌, eeeee eeeeeeeeeeee eeee eee eeeeeeee eeeeeee eee ee eeeeeeee ee eeeeeeeeeeeeeeeee eeee eeeeeee (‌Meeeee 8‌).[‌88‌]

‌Meeeee 8‌ Me Meeeeee ee eee Meeeeeeee Meeeeeee[‌88‌]

Me eee eeeee ee eeeee eeee,[‌88‌] eee eeeeeeee eeeee eeeeeeeeeeeee eeeeee ee eee eeeeeee ee eeee eee eeee eeeeeeee eeee eeeee eeeeee eeee ee eeeeeeee; eeeeeee, eee eeeeeeeeeee ee eeeeeeeeeeee eeeeeeeeeeee eeee eeeeeeee 88.8% eeeee ee eeeee 8-eeeeee-8-eee-8-eeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeeeeeeeeee (‌8‌).

Mee eeeeeeee eeeeeeeee eeeeeeee ee eee eeeeeeeeee[‌88‌] eee eee Meeeeeeee eeeeeeee eeeeeeee eeeeeeeee ee ee eeeeeee eee ‌8‌ eeeee eeeeee eeee eee 8,8-eeeeeeeeee eeeeeeeee ee eeeeeee ee eeeeeeeeeeee ‌8‌, eeeee eeeee eeeeeeeeee eeeeeeeeeee eee eeeeeeeeeee eeeeeeee eee Meeeeeeee eeeeeee ‌8‌ (‌Meeeee 8‌).

Meee eeeeeeeeeeee eee eeee (8 eeeee) eeeee eeeee eeeeeee eeeeeeeeee (MeMM/MMe) ee eeee eeeeeeeeeee, eeeeeeeee ‌8‌ eeeeeeeeeeee eeee eee eeeeeeee eeeeee 88–88 eeeeeee. Meeeeee, eeee eeee eeeeeeee ee eeeeeee eee ee eee eeeeeeee ee eeeee eeeeeeeeeeee eeeee eeeeeeeee eeeeeeeee eeeeeeee eeeeeeeeee, eeeeeeeee ‌8‌ ee eee eeeeee, eee 8,8,8,8-eeeeeeeeeeeeeeeeeeee ‌8‌ eeeeee ee eeeeeeeeeee eeeeee eeee eee eeeeeeee eeeeeee eeeeee 8–8 eeeee (eeeeeeee eeeeeeeeee eeeee 8–8 eeee). Mee eeeeeeeeeee eeeeeeeee eee eeeeeeee eeeeeeeeeeee ‌8‌ eee eeee eeeeeeeeeeee ‌8‌ eeee eee eeeeeeeeee e eeeee eeeeeee; eeeeeee, eeeee eeeeeee ee eeeee ‌8‌ eee eeeeeeeee eeeeeeee ee eeeeeeeee.[‌88‌]

‌Meeeee 8‌ Mee Meeeeeee Meeeeeeee ee eee Meeeeeeee Meeeeeee[‌88‌,‌88‌]

Meee, eee eee eeeeeeee eeee ee eee eeeeeeeee ee eeeeeee eeeeee ‌8‌. Meee e eeeeeeeeeee eeeeeeeee, eee eeeeee eee eeeeee eeeeeeeeeee ee eee Meeeeeeee eeeeeeee eeeeee ee eeeeeee ee eeeeeeee eeeeeeeeee eeeeeeee eeeeeeeee ee eeee eeeeeeeeeeee, eeeeeeeee eee ee eeeeeeee, eeeeeeee, ee eeeeeeeee eeee eee eeeeeeeeeeee eeeeeeeee ee.

References