Synthesis and reactions of some dihydro and tetrahydro‐4 H ‐imidazo[5,4,1‐ ij ]quinoline derivatives | Zendy

Saari Walfred S. | Zendy; Halczenko Wasyl | Zendy; Freedman Mark B. | Zendy; Arison Byron H. | Zendy

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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.

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