3 COMPLEMENTARY METHODS OFFERING ACCESS TO 5-SUBSTITUTED 1,2,3,4-TETRAHYDROISOQUINOLINES

Authors
SCHLOSSER M SIMIG G GENESTE H
Citation
M. Schlosser et al., 3 COMPLEMENTARY METHODS OFFERING ACCESS TO 5-SUBSTITUTED 1,2,3,4-TETRAHYDROISOQUINOLINES, Tetrahedron, 54(31), 1998, pp. 9023-9032
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
31
Year of publication
1998
Pages
9023 - 9032
Database
ISI
SICI code
0040-4020(1998)54:31<9023:3CMOAT>2.0.ZU;2-M
Abstract
The scope and limitations of three independent though related routes l eading to 5-substituted tetrahydroisoquinolines are explored : the Pid et-Spengler type cyclization of ortho-substituted 2-phenylethylamines, the Pomeranz-Fritsch type cyclization of meta-substituted benzylamine s and the electrophilic trapping of 5-lithiated 4-lithiooxytetrahydroq uinolines. The introduction of the substituent relies in all three cas es on a neighboring group assisted site selective metalation step. (C) 1998 Elsevier Science Ltd. All rights reserved.