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Synthesis of a novel series of 3‐substituted [1]benzothieno[3,2‐d]pyrimidine derivatives
Author(s) -
ElTelbany Farag,
Hutchins Robert O.
Publication year - 1985
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.5570220236
Subject(s) - chemistry , boron trifluoride , pyrimidine , yield (engineering) , medicinal chemistry , formaldehyde , mannich reaction , aryl , alkyl , organic chemistry , condensation , stereochemistry , catalysis , materials science , physics , metallurgy , thermodynamics
A series of 3‐substituted [1]benzothieno[3,2‐ d ]pyrimidine derivatives has been synthesized as possible antileukemic agents by condensation of methyl 3‐(ethoxymethylene)amino‐2‐benzothiophene carboxylate (II) with a variety of amines to afford the corresponding 3‐aryl and 3‐alkyl [I]benzothieno[3,2‐ d ]pyrimidin‐4(3 H )‐ones, Ill and IV, respectively. In addition, Mannich reactions of [I]benzothieno[3,2‐ d ]pyrimidin‐4(3 H )‐one (VIII) with formaldehyde and secondary amines gave the expected derivatives, IX. 3‐Amino[I]benzothieno[3,2‐ d ]‐pyrimidin‐4(3 H )‐one (VI) reacted with substituted aromatic aldehydes in the presence of boron trifluoride to yield the corresponding imines VII.