Premium
Synthesis and nuclear magnetic resonance spectra of fused pyrimidines
Author(s) -
AlJallo Hikmat N.,
Muniem Muhamad A.
Publication year - 1978
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.5570150525
Subject(s) - chemistry , benzothiazole , thiazole , benzimidazole , yield (engineering) , thiazoline , proton nmr , spectral line , nmr spectra database , proton , stereochemistry , organic chemistry , materials science , physics , quantum mechanics , astronomy , metallurgy
Ethy phenylpropiolate reacted with 2‐aminobenzothiazoles, benzimidazoles, thiazoline and thiazole to give the corresponding fused 2‐oxopyrimidines. 2‐Mercaptobenzimidazole reacted with ethyl phenylpropiolate to give 4‐phenyl‐2 H ‐1‐thiapyrimido(1,2‐ a ]benzimidazol‐2‐one in very good yield. The thiones, methylthio iodides and the hydrobromides of some of the products were prepared. Analysis of the nmr spectra of the benzothiazole and benzimidazole products and their 3‐deuterio analogs showed that the proton at position 6 is shielded and absorbs together with the proton at position 3 near δ 6.0 ppm. The nmr and ir spectral data of all the products are tabulated and discussed.