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Preparation of 1,3‐disubstituted isoquinoline derivatives from N ‐boc‐3‐substituted‐1,2‐dihydroisoquinolines
Author(s) -
Clark Robin D.
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320115
Subject(s) - chemistry , isoquinoline , sodium borohydride , electrophile , tetrahydroisoquinoline , alkylation , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis
3‐Substituted N ‐Boc‐1,2‐dihydroisoquinolines 2 can be functionalized at the 1‐position via lithiation and subsequent electrophilic trapping. The resulting products 3 can be deprotected and oxidized to afford the corresponding 1,3‐disubstituted isoquinolines 5 . Deprotection of dihydroisoquinoline 3k followed by sodium borohydride reduction affords the cis ‐1,3‐disubstituted tetrahydroisoquinoline 11 . The 1,3‐disubstituted N ‐Boc‐1,2‐dihydroisoquinoline 3g is efficiently alkylated at the 1‐position to give 1,1,3‐trisubstituted analogs 12 .