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The synthesis of benzofuroquinolines. V . Some benzofuro[3,2‐ B ]quinoline derivatives
Author(s) -
Yamaguchi Seiji,
Tsuzuki Kunihiro,
Sannomiya Yoshie,
OhHira Yutaka,
Kawase Yoshiyuki
Publication year - 1989
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.5570260204
Subject(s) - chemistry , quinoline , benzoic acid , benzaldehyde , medicinal chemistry , condensation , isatin , derivative (finance) , chloride , stereochemistry , organic chemistry , physics , financial economics , economics , thermodynamics , catalysis
Some benzofuro[3,2‐ b ]quinoline derivatives 1a‐d and 3a were synthesized by condensation of 2‐amino‐benzaldehyde, 2‐aminoacetophenone, 2‐aminobenzophenone, isatin, or 2‐aminobenzoic acid with 3(2 H )‐benzofuranone. The benzofuroquinolinone 3a was also obtained from 2‐aminobenzoic acid and phenoxy‐acetyl chloride in two steps and converted to 10‐chloro derivative 1e . Similarly, some 8‐halobenzofuro[3,2‐ b ]‐quinoline derivatives 1d,e and 3a (X = F, Cl, Br, I) were synthesized from 5‐haloisatin or 2‐amino‐5‐halo‐benzoic acid. And benzofuro[3,2‐ b ]quinolines 1a‐e thus obtained were converted to corresponding N ‐oxides 2 .