Addition of alkyllithiums to 3 H -quinazoline-4-thione and various substituted quinazoline derivatives; application in synthesis.

Autor:	Smith, Keith, El-Hiti, GamalA., Hegazy, AmanyS.
Předmět:	QUINAZOLINE CHEMICAL reactions PHENYL compounds MOLE (Chemistry) MOLECULAR theory
Zdroj:	Journal of Sulfur Chemistry; Apr2005, Vol. 26 Issue 2, p121-129, 11p, 4 Diagrams, 4 Charts
Abstrakt:	Reaction of 3 H -quinazoline-4-thione (1) with two mole equivalents of an alkyllithium ( t -BuLi, n -BuLi or MeLi) at-78 ° C in dry THF gave the corresponding 2-alkyl-1,2-dihydro-3 H -quinazoline-4-thione (4, 5 or 6) in high yield. Similarly, reactions of 4-(methylthio)quinazoline (7), 4-(ethylthio)quinazoline (8) and 4-methoxyquinazoline (9) with alkyllithiums (one mole equivalent) gave the corresponding 4-substitued 2-alkyl-1,2-dihydroquinazolines 11–18. On the other hand, blocking position 2 with a phenyl group in 4-(methylthio)-2-phenylquinazoline (20) and 4-methoxy-2-phenylquinazoline (21) resulted in reaction with two mole equivalents of alkyllithiums to give 4,4-dialkyl-2-phenyl-3,4-dihydroquinazolines 22–24. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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