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Cycloaddition of Aroyl Isothiocyanate: A Novel Synthesis of Triazine, Oxazine, Pyrimidine, and Pyridine Derivatives
Author(s) -
Assy Mohamed G.,
ElSayed Hassan A.,
Ouf Nabil H.,
Hamza Ahmed,
Morsy Hesham A.
Publication year - 2019
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.3690
Subject(s) - chemistry , hydrazine (antidepressant) , malononitrile , phenyl isothiocyanate , hydrate , acetylacetone , pyridine , isothiocyanate , pyrimidine , organic chemistry , condensation reaction , urea , medicinal chemistry , catalysis , stereochemistry , chromatography
A simple and direct synthetic methodology for a novel series of azines and their annulated systems was performed. Heterocyclization of acyl isothiocyanate 2 with urea or malononitrile gave s ‐triazine 4 and 1,3‐oxazine 7 derivatives, respectively. The reaction of heteroallene 1 with acetylacetone tolerated 2‐thioxopyridine derivative 9 . The latter compound underwent heterocyclization with urea, hydrazine hydrate, or phenyl hydrazine to give the annulated pyridines 10 – 12 . Pyrimidinethione 14 was resulted from reaction of acylisothiocyanate with enamine 13 . Condensation of compound 14 with hydrazine hydrate, phenyl hydrazine, urea, and 3‐nitrobenzaldehyde in the presence of ethyl cyanoacetate or sodium hydroxide afforded 15 – 20 , respectively.