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

Article abstract of DOI:10.1248/cpb.46.508

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.

Full text of DOI:10.1248/cpb.46.508

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