Tetrahedron p. 5185 - 5196 (1984)
Update date:2022-08-03
Topics:
Meijer, Louis H. P.
van Niel, Johannes C. G.
Pandit, Upendra K.
N-(Cyclopropylmethylene)phenylamines (1a-c), cyclopropyl 2-pyridyl ketones (5a-c) and ethyl cyclopropylmethylenepyruvate (14) have been subjected to reduction by 1,4-dihydropyridines <3,5-diethoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine (2) and/or 1-benzyl-1,4-dihydronicotinamide (7)> in the presence of magnesium ions, and by tin hydrides.The reactions with 1,4-dihydropyridines do not involve cleavage of the three-membered ring in the reduction step.The observed acyclic product from 2-pyridyl 2,2-dimethylcyclopropyl ketone (5b) is a consequence of ring cleavage prior to reduction of the carbonyl function.In contrast, reduction of 1a-c and 5a-c by tin hydrides leads to products in which the cyclopropane moiety has undergone ring-opening.These findings support a hydride transfer mechanism for reductions with NADH models.
View MoreContact:+86-535-8888888
Address:No.161 Haishi Rd.
Qida Chemical Co., Ltd.(expird)
Contact:+86-25-8776 0031
Address:3-2001 Jiaye Int'l Town, 158 Lushan Road,Nanjing, 210019, China
Tianjin Hedong Red Cliff Chemical Reagent Factory
Contact:+86-022-84780548
Address:Li Ming Zhuang Gong Ye Yuan,Dongli District,Tianjin,China
Rizhao Lanxing Chemical Indusrial Co.,Ltd
Contact:86-633-2616708
Address:NO.15 West road Shenglan, Lanshan district, Rizhao City
Contact:+91 9963263336
Address:Plot#146A, IDA Mallapur, Hyderabad - 500072
Doi:10.1016/j.bmc.2007.06.016
(2007)Doi:10.1002/ejic.200600599
(2006)Doi:10.1016/j.jcat.2007.06.007
(2007)Doi:10.1016/S0040-4039(00)96630-9
(1987)Doi:10.1016/j.carres.2007.06.004
(2007)Doi:10.1021/ja01150a041
(1951)