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 hide the growth in pyridazine chemistry given that 1979, the date in their past ebook in quantity 24 of Advances.Professor Vorbruggen of Berlin has contributed a survey of the amination of nitrogen heterocycles, which offers quite with aminations within which an ami no workforce replaces another performance at the heterocyclic ring. hence, this evaluation enhances our contemporary evaluation in quantity forty four facing the Tschitschibabin response, within which a hydrogen atom at the heterocyclic ring is changed by means of an amino group.The different 3 chapters within the current quantity all care for bicyclic heterocycles. Dr. H. okay. Pujari of Kurukshetra college in India describes condensed 4-thiazolidinones, and Professor M. A. E. Shaban and A. Z. Nasr of Alexandria collage 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 sooner than.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 49
On the other hand, acids 289a-g, obtained from thiones 288a-g and chloroacetic acid, on cyclization with acetic anhydride in pyridine or Dowtherm-A give, both isomers 290a-g and 291a-g [81CPB1876; 86IJC(B)807;87UPSl; although it was earlier reported that acid 289a-d, on cyclization with acetic anhydride in pyridine, yielded only one isomer for which structures, 290a,291b,290c and 290d were assigned on the basis of 'H-NMR spectroscopy [70IJC10; 72IJC274; 731JC1119; 781JC(B)478]. Acid 289e gave both isomers 290e and 291e which could not be separated, but their identities were confirmed by 'H-NMR spectral data (74TH1).
A The bicyclic compounds obtained from unsymmetrical pyrimidinethiones (104,107, and 110) can be represented by either structures 105 or 106 (50BRP634951), 108 or 109 (83M13), and 111 or 112 (75FRP223371, 75GEP2317109; 76JAP74126828), respectively (Scheme 24). No characterization of the cyclized products was attempted although cyclized product obtained from 104 was used in the preparation of merocyanine dyes (50BRP634952). 4,6,6-Trimethyl- 1,6-dihydropyrimidine-2-thione(113),on condensation with aromatic aldehydes in ethanolic KOH, gives arylidene derivatives 114 which react with chloroacetic acid in the presence of anhydrous sodium acetate in acetic anhydride to afford a cyclized product formulated as 115 (81MI1) that can also be represented by the alternate structure 116 (Scheme 25).
PUJARI [Sec. 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.