Advances in Heterocyclic Chemistry, Vol. 49 by Alan R. Katritzky (Ed.)

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 college of Ljubljana, Yugoslavia disguise the development in pyridazine chemistry when you consider that 1979, the date in their earlier e-book in quantity 24 of Advances.Professor Vorbruggen of Berlin has contributed a survey of the amination of nitrogen heterocycles, which offers really with aminations during which an ami no workforce replaces another performance at the heterocyclic ring. hence, this overview enhances our contemporary evaluation 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 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 coated 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 resources for Advances in Heterocyclic Chemistry, Vol. 49

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SCHEME 30 24 HRUSHI K. PUJARI [Sec. A 10. Thiazolo[2,3-c][1,2,4]benzothiadiazin-3(2H)-ones The synthesis of a thiazolo[2,3-c][ I ,2,4]thiadiazin-3(2H-one has so far not been reported. However, the synthesis of its benz-analog (144) has been achieved as illustrated in Scheme 31. However, when the cyclization was carried out in acetic anhydride without pyridine, a different compound identified by spectral data as 6-chloro-2-(ahydroxyethylidene) thiazolo[2,3-~][I ,2,4]benzothiadiazin-3(2H)-one-9,9dioxide acetate (143a) was obtained.

Cyclization of 2-(phenacylthio benzimidazoles, obtained from the reaction of unsymmetrical benzimidazolyl-2-thiones (282) with phenacyl halides can give rise to two isomeric cyclized products, depending on the nitrogen atom involved in the ring closure. No systematic studies on the orientational preference shown by substituents in the benzene ring during the cyclization leading to the synthesis of 3-arylthiazolo[3,2a]benzimidazoles have been made, probably because of the difficulties of establishing the position of substituents in the benzimidazole nucleus.

The other possible isomeric structure 241 could also represent the cyclized product. (237) SCHEME 58 Sec. Al CONDENSED 4-THIAZOLIDINONES 41 SCHEME 59 29. Thiazolo[3,2-a]indol-3(2H)-ones Synthesis reported by American workers of the reaction of y-oxo-indolI-butanoic acids with thionyl chloride serves as a convenient method for this relatively inaccessible tricyclic system (79JOC3994). The reaction of y-oxo-3-[ (methoxycarbonyl)methyl]indol-I-butanoic acid (242a) with thionyl chloride followed by treatment with methanol gives (Z)-methyl 2,3-dihydro-2-(2-methoxycarbonylethylidene)-3-oxo-thiazolo[ 3,2-a]indol9-acetate (243a).

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