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 development in pyridazine chemistry considering 1979, the date in their earlier ebook in quantity 24 of Advances.Professor Vorbruggen of Berlin has contributed a survey of the amination of nitrogen heterocycles, which offers relatively with aminations during which an ami no team replaces another performance at the heterocyclic ring. hence, this evaluate enhances our contemporary evaluate in quantity forty four facing the Tschitschibabin response, within which a hydrogen atom at the heterocyclic ring is changed via an amino group.The different 3 chapters within the current quantity all take care of 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. ultimately, Professor T. A. Crabb of Portsmouth, England has lined saturated bicyclic 6/5 ring-fused structures with a bridgehead nitrogen and a unmarried extra heteroatom. None of those teams of bicyclic heterocycles has been comprehensively reviewed earlier than.
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 49
12. Thiazolo[2,3-c]-[ 1,2,4]benzotriazin-3(2H)-ones 2,3-Dihydro-l,2,4-benzotriazine-3-thiones (171a,b) react with halogenoacid in the presence of fused sodium acetate in anhydrous ethanol to (165 1 (166 1 (167) SCHEME 36 (168) Sec. ph,_m-MeCsH~,cH*ph,NHPh. SCHEME 31 give the acids 172a,b which, on treatment with acetic anhydride and pyridine, furnish cyclized products. 2-6]-[ I ,2,4]-benzotriazin-3(2H)-one (174),was assigned to the cyclized products because of the chemical shifts of HA in 175 obtained from the reaction of 171 and I ,2-dibromoethane.
Proton HA in 284e-g,ij resonates downfield when compared to that in 286eg , i j (or 287e-g,ij), while HA in 285e-g,ij resonates at approximately the same position as that in 286e-g,ij (or 287e-g,ij). This deshielding has its origin in the magnetic anisotropy of the carbonyl group with little contribution from the rest of the ring. The second approach concerns the comparative studies of the observed and calculated chemical shifts of the aromatic protons of cyclized products 284 or 285 and 290 or 291.
A] 21 CONDENSED 4-THIAZOLIDINONES (113 1 (117 1 SCHEME 25 (118 formed only in 10 percent yield. The mixture was resolved by column chromatography. When the reaction was carried out in the presence of boron trifluoride etherate in methanol, the cyclized compound 120 was the only isolable product [87IJC(B)556]. 73) in the cyclized product 120 (R = Ph) when compared to that in 119 (R = Ph). Such a downfield shift of H A is not expected from alternative structure 122 (Scheme 26). Thiones 123 react with chloroacetic acid in the presence of anhydrous sodium acetate in acetic acid and acetic anhydride to give a cyclized product for which structure 124 has been assigned (82MII).