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Synthesis and reactions of some dihydro and tetrahydro‐4 H ‐imidazo[5,4,1‐ ij ]quinoline derivatives
Author(s) -
Saari Walfred S.,
Halczenko Wasyl,
Freedman Mark B.,
Arison Byron H.
Publication year - 1982
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.5570190426
Subject(s) - chemistry , sodium borohydride , sodium azide , quinoline , medicinal chemistry , carbamate , double bond , stereochemistry , organic chemistry , catalysis
Reaction of phenyl N ‐(8‐quinolinyl)carbamate with sodium borohydride afforded 1,2‐dihydro‐4 H ‐imidazo‐[5,4,1‐ ij ]quinolin‐2‐one, 2a . The 5,6‐double bond of 2a was functionalized by reaction with nitrosyl chloride to give the nitroolefin 4 and by reaction with hypobromous acid to give the trans ‐bromohydrin 5 . Reaction of 5 with sodium azide led to the rearranged trans ‐6‐azido‐5‐ol 7 , the structure of which was determined by 1 H nmr studies.