By Alan R. Katritzky (Ed.)
(from preface)Volume forty nine of Advances in Heterocyclic Chemistry includes 5 chapters. Professors M. Tiller and B. Stanovnik of the collage of Ljubljana, Yugoslavia conceal the development in pyridazine chemistry due to the fact 1979, the date in their earlier book in quantity 24 of Advances.Professor Vorbruggen of Berlin has contributed a survey of the amination of nitrogen heterocycles, which offers rather with aminations within which an ami no crew replaces another performance at the heterocyclic ring. hence, this evaluation enhances our fresh evaluate in quantity forty four facing the Tschitschibabin response, within 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. okay. 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. eventually, 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 prior to.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 49
The synthesis of 249a from 250, obtained from the thione 247 and chloroacetaldehyde, fixes the position of the hydroxyl group at the 3-position in 250 which, on dehydration Sec. I I A I CONDENSED 4-THIAZOLIDINONES 43 with phosphoryl chloride in pyridine, gives thiazolo[3,2-~]benzimidazole (251). This establishes unambiguously the involvement of sulfur rather than nitrogen in the condensation reaction between the thione 247 and a-halogenocarbonyl compounds. Reaction of 247 with chloroacetic acid in the presence of sodium acetate in ethanol gave a product with a melting point of 212°Cformulated as 249a (60MII;61UKZ503)which, on treatment with hydrochloric acid, yielded a compound with a melting point of 182°C for which structure 2,4thiazolidinedione (252) was assigned (61UKZ503)without any evidence.
A H (2421 a. RzCO2Me 1 b, R'=H (243) a, R1=C02Me,R2=Me b, R1=H, R2=Me C , R1= H , R2=CH~CMe3 ( 244) SCHEME60 30. Thiazolo[3,2-a]benzimidazol-3(2H)-ones The synthesis of thiazolo[3,2-a]benzimidazol-3(2H)-one (249a) was first reported by Stephen and Wilson (26JCS2531; 29MI1) in 25% yield by cyclization with metallic sodium in refluxing benzene of ethyl/methyl benzimidazo-2-thiolacetate(248, R = H, R' = EtlMe) obtained from benzimidazolyl-2-thione (247) with ethyVmethy1 chloroacetate. Later, Duffin and Kendall(50BRP63495 1 ;5 1JCS734; 56JCS361) obtained 249a in 64% yield by the cyclodehydration of the acid 248 (R = R' = H)with acetic anhydride in pyridine.
Al 53 CONDENSED 4-THIAZOLIDINONES (84JIC89). The most downfield signal was wrongly considered to be due to H-5in 284b, as it is deshielded by the carbonyl group and such a downfield signal was not possible from the alternate structure 285b. In fact, the most downfield signal in 28413 would be due to H-7 because of the deshielding effect of the nitro group on the ortho proton (H-7). A nitro group deshields ortho protons to a greater extent than meta or para protons (69MI1), and this value is much greater than that obtained from the deshielding effect of the carbonyl group.
Advances in Heterocyclic Chemistry, Vol. 49 by Alan R. Katritzky (Ed.)