By Alan R. Katritzky (Ed.)
(from preface)Volume forty nine of Advances in Heterocyclic Chemistry comprises 5 chapters. Professors M. Tiller and B. Stanovnik of the college of Ljubljana, Yugoslavia disguise the growth in pyridazine chemistry on account that 1979, the date in their past book in quantity 24 of Advances.Professor Vorbruggen of Berlin has contributed a survey of the amination of nitrogen heterocycles, which offers relatively with aminations within which an ami no staff replaces another performance at the heterocyclic ring. hence, this assessment enhances our fresh evaluation in quantity forty four facing the Tschitschibabin response, during which a hydrogen atom at the heterocyclic ring is changed through an amino group.The different 3 chapters within the current quantity all care for bicyclic heterocycles. Dr. H. ok. Pujari of Kurukshetra collage in India describes condensed 4-thiazolidinones, and Professor M. A. E. Shaban and A. Z. Nasr of Alexandria college in Egypt survey the synthesis of condensed 1,2,4-triazolo heterocycles. ultimately, Professor T. A. Crabb of Portsmouth, England has lined saturated bicyclic 6/5 ring-fused platforms with a bridgehead nitrogen and a unmarried extra heteroatom. None of those teams of bicyclic heterocycles has been comprehensively reviewed sooner than.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 49
Al 23 CONDENSED 4-THIAZOLIDINONES (135) (136) (137) SCHEME 29 b. From u Thiuzok. There are only two instances that describe the synthesis of thiazolo[3,2-a]pyrimidin-3(2H)-ones through this route. 5 3 Dimethyl-2-imino-4-thiazolidinone (132)reacts with alkylmalonyl chloride to give the acids 133 which, on pyrrolytic dehydration, furnish 2,2-dimethyl-6-alkyl-4,5,6,7- tetrahydro-2H- thiazolo[3,2-a]pyrimidin-3,5,7triones (134) (5OJCSl 127). A better result is obtained by heating the acid in a vacuum.
R=H b , R =CH$CH2)3 SCHEME48 36 HRUSHl K. PUJARl (2121 [Sec. l l . A (210 1 a , X=C(Me)NHPh b, X=O (211 ) 0 ,R - H b , RZMe SCHEME 49 19. Thiazolo[3,2-a]-[l,3]diazocin-3(2H)-ones Dehuri and Nayak (83JIC970) reported that 3,4,5,6,7,8-hexahydro1,3-diazocine-2-thione (213), obtained from I ,5-dibromopentane and thiourea in boiling ethanol, reacts with chloroacetic acid or its ethyl ester followed by basification to give 5H-6,7,8,9-tetrahydrothiazolo[3,2-a][ 1,3]diazocin-3(2H)-one(214). The reaction of 213 with ethyl chloroacetate was not smooth and the yield was low.
I ,2,4-triazine nuclei can be affected in two ways represented by thiazolo[2,3-c]-[1,2,4]-triazin-3(2H)-one (148) and thiazolo[3,2-6]-[ 1,2,4]triazin-3(2H)-one (157). Synthesis of both the systems have been accomplished by building the I ,2,4-triazine nucleus onto the thiazolidinone nucleus or vice-versa. i. ~. 2-Hydrdzino-4-thiazolidinone (146, R = H) reacts with chloroacetic anhydride to afford 147 which, on pyrrolysis, readily cyclizes to give 2H,7H-5,6-dihydrothiazoIo[2,3-c]-[I ,2,4]-triazin-3,6-dione (148) (72ZOR1722).