Department of Applied Chemistry, University of Mohaghegh Ardabili, P.O. Box 56199-11367, Ardabil, Iran.
Mol Divers. 2018 Nov;22(4):907-917. doi: 10.1007/s11030-018-9844-1. Epub 2018 Jun 27.
Four-component reaction between primary amines, dialkylacetylendicarboxylates, tetrazolo[1,5-a] quinoline-4-carbaldehyde and ethyl-2-cyanoacetate in the presence of 1,4-diaza-bicyclo[2.2.2]octane and zinc oxide nanoparticles results to the regioselective production of new tetrazolo[1,5-a]quinoline-based 2-amino-1,4-dihydropyridine or pyridin-2(1H)-one derivatives in good to high yields. The selectivity of the catalyzed reaction toward the generation of the dihydropyridine or pyridin-2(1H)-one derivatives was found to be strongly dependent on the size of the alkyl groups in the ester moieties of the acetylenic esters. According to single-crystal X-ray diffraction and NMR studies, the pyridin-2(1H)-one derivatives involve a restricted rotation around the C-C bond connecting the tetrazoloquinoline and dihydropyridinone cyclic systems.
在 1,4-二氮杂双环[2.2.2]辛烷和氧化锌纳米粒子的存在下，伯胺、二烷基乙酰二羧酸酯、四唑并[1,5-a]喹啉-4-甲酰腙和乙基-2-氰基乙酸酯之间发生四组分反应，以高产率至极好产率地对映选择性地生成基于四唑并[1,5-a]喹啉的新的 2-氨基-1,4-二氢吡啶或吡啶-2(1H)-酮衍生物。发现催化反应对二氢吡啶或吡啶-2(1H)-酮衍生物的生成的选择性强烈依赖于炔属酯的酯部分中的烷基基团的大小。根据单晶 X 射线衍射和 NMR 研究，吡啶-2(1H)-酮衍生物涉及围绕连接四唑并喹啉和二氢吡啶酮环系的 C-C 键的受限旋转。
