Synthesis of benzyl substituted tetrahydropyridines and 1,2,3,4-tetrahydroisoquinolines via acid catalyzed cyclization of γ,δ-unsaturated N-formyl-N-styryl amines

Add time:07/25/2019    Source:sciencedirect.com

Acid-catalyzed cyclization of N-(3-methylbut-3-enyl)-N-styrylformamides 1–3 in the presence of 9-BBN triflate gave access to 2-benzyl-1-formyl-4-methyl-1,2,5,6-tetrahydropyridines 4a–6a and minor amounts of the isomeric 1,2,3,6-tetrahydropyridines 4b–6b. Triflic acid catalyzed cyclization of N-2-(arylethyl)-N-styrylformamides 7, 8 gave the corresponding 1-benzyl-2-formyl-1,2,3,4-tetrahydroisoquinolines 9 and 10.

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