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The first synthesis of thieno[ c ]isoquinolines and an improved synthesis of phenanthridine and thieno[ c ]quinolines through pd(0) catalyzed coupling of ortho ‐formylarylboronic acids with functionalized aryl halides
Author(s) -
Yang Youhua,
Hörnfeldt AnnaBritta,
Gronowitz Salo
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.5570260366
Subject(s) - phenanthridine , chemistry , catalysis , nuclear magnetic resonance spectroscopy , nmr spectra database , chemical shift , stereochemistry , carbon 13 nmr , medicinal chemistry , spectral line , organic chemistry , physics , astronomy
Abstract All three isomeric hitherto unknown thieno[ c ]isoquinolines have been synthesized in high yields by the Pd(0)‐catalyzed coupling of 2‐formylbenzeneboronic acid with t ‐butyl‐ N ‐( ortho ‐halothienyl)carbaniates. When 2‐bromoacetanilide, instead of 2‐bromoaniline, was coupled with orth ‐formylarylboronic acids under Pd‐catalysis, phenanthridine and thieno[ c ]quinolines were obtained in improved yields. Total assignments of 1 H nmr spectra of thieno[ c ]isoquinolines and thieno[ c ]quinolines are reported. Assignments are based on high resolution 300 MHz 1 H nmr spectra, two‐dimentional 1 H‐ 13 C chemical shift correlation spectra and one‐dimentional INADEQUATE 13 C nmr spectroscopy.