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

Authors
Meuzelaar, GJ Maat, L Sheldon, RA
Citation
Gj. Meuzelaar et al., Synthesis of benzyl substituted tetrahydropyridines and 1,2,3,4-tetrahydroisoquinolines via acid catalyzed cyclization of gamma,delta-unsaturated N-formyl-N-styryl amines, TETRAHEDRON, 55(14), 1999, pp. 4481-4488
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
14
Year of publication
1999
Pages
4481 - 4488
Database
ISI
SICI code
0040-4020(19990402)55:14<4481:SOBSTA>2.0.ZU;2-1
Abstract
Acid-catalyzed cyclization of N-(3-methylbut-3-enyl)-N-styrylformamides 1-3 in the presence of 9-BBN triflate gave access to 2-benyl-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-(ary lethyl)-N-styrylformamides 7, 8 gave the corresponding 1-benzyl-2-formyl-1, 2,3,4-tetrahydroisoquinolines 9 and 10. (C) 1999 Elsevier Science Ltd. All rights reserved.