Synthesis of N,N-Dimethyl-2-(tributylstannyl)methyl-5-substituted Benzylamines as a Quinodimethane Precursor by the Reaction of N,N-Dimethyl-N-(tributylstannyl)methyl-4-substituted Benzylammonium Salts with Lithium Diisopropylamide.
作者:Yasuhiro MAEDA、Yoshiro SATO
DOI:10.1248/cpb.46.508
日期:——
Reaction of N, N-dimethyl-N-(tributylstannyl)methyl-4-substituted benzylammonium salts 2 with lithium diisopropylamide (LDA) gave N, N-dimethyl-2-(tributylstannyl)methyl-5-substituted benzylamines 3 as the main products. Treatment of 3 with iodomethane followed by tetrabutylammonium fluoride (TBAF) in the presence of dimethyl fumarate gave the corresponding dimethyl trans-1, 2, 3, 4-tetrahydro-6-substituted naphthalene-2, 3-dicarboxylates 15 in good yields.
N, N-二甲基-N-(三丁基锡)甲基-4-取代苄基铵盐 2 与二异丙基酰胺锂(LDA)反应,得到主要产物 N, N-二甲基-2-(三丁基锡)甲基-5-取代苄胺 3。用碘甲烷处理 3,然后在富马酸二甲酯存在下用四丁基氟化铵(TBAF)处理,可以得到相应的反式-1,2,3,4-四氢-6-取代萘-2,3-二甲酸二甲酯 15,收率很高。