G. M. El-Naggar

SYNTHESIS AND REACTIONS OF SOME ISOQUINOLINE DERIVATIVES

Abstract Treatment of 3,4-tetramethylene-6-amino-5-cyano-thiopyran-2(1H)thione (1) with alkali followed by acidification with HCl afforded 1,2,5,6,7,8-hexahydro-4-cyano-3(2H)-oxoisoquinoline-1-thiol (2). When compound (1) was reacted with excess alkyl halides the corresponding O- and S-alkylated isoquinolines (3) were obtained. Also, α-chloroacetic acid and β-bromopropionic acid reacted with compound (2) to produce thiazolo and thiazinoisoquinoiines (4) and (5). Furthermore, the reaction of (2) with one mole of phenacylbromide produced-S-phenacyl derivatives (6), which cyclized to give the corresponding thiazoloisoquinoline (7). However two moles of phenacyl bromides gave the corresponding S- and O-phenacyl derivatives (8). The later compounds were cyclized to give furoisoquinoline derivative (9).

Synthesis and Reactions of Some New Thienopyrimidines

4-Methyl-6-mercapto-2-phenylpyrimidine-5-carbonitrile ( 1 ) was reacted with different halo compounds, namely ethylchloroacetate, chloroacetone, bromoacetanilide, p-chlorobromoacetanilide, and p -methoxy chloroacetanilide in ethanol in the presence of sodium acetate yielded the corresponding S-alkylated derivatives ( 2a-e ). The latter compounds underwent cyclization into thienopyrimidines ( 4a-e ) upon treatment with sodium ethoxide in ethanol. The reaction of ( 4a ) with hydrazine hydrate led to the formation of 5-amino-4-methyl-2-phenylthieno[2,3-d]pyrimidine-2-carbohydrazide ( 5 ). Compound ( 5 ) was reacted with a variety of reagents to produce other new thienopyrimidines as well as oxadiazolylthienopyrimidines ( 6, 11 ).

SYNTHESIS OF TRICYCLIC COMPOUNDS WITH THIOPYRIDONE RINGS

Abstract Reaction of 3,4-trimethylene-6-amino-5-ethoxycarbonylthiopyrane-2-thione (1) with hydrazine hydrate gave the corresponding o-diaminocyclopentapyridine-2-thione (2). Ring closure of 2 with some reagents, namely, formic acid, aromatic aldehydes, carbon disulphide. phenacyl bromide, ethyl chloroformate, ethyl chloroacetate, nitrosylsulfuric acid, and pyruvic acid gave tricyclic compounds (2–14) by direct or indirect pathways, respectively.