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 considering 1979, the date in their prior book in quantity 24 of Advances.Professor Vorbruggen of Berlin has contributed a survey of the amination of nitrogen heterocycles, which offers fairly with aminations within which an ami no staff replaces another performance at the heterocyclic ring. hence, this evaluate enhances our contemporary overview 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 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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22. 10, I I-hexahydro-5H-thiazolo13,2,-~]-[ I ,3]diazecin-3(2H)-one(223). As in earlier cases, the reaction of CHR (2201 SCHEME 52 (2211 HRUSHI K. PUJARI 38 [Sec. A 222 with ethyl chloroacetate was not smooth and the yield was low. which are also obtained from 223 and aldehydes (83JIC970)(Scheme 53). Thiazolidinone structures 223 and 224 have not been characterized by spectral data. 23. Thiazolo[3,2-a]-[l,3]diazacycloundecan-3(2H)-ones 1,3-Diazacycloundecane-2-thione(225) reacts with chloroacetic acid or its ethyl ester to give thiazolo[3,2-a]-[ 1,3]-diazacycloundecan-3(2H)-one (226).
R=aryl b, d= NHAc. R=aryl b,R1=NHAc SCH€ME 70 54 HRUSHI K . PUJARI [Sec. A by steric factors only. Thus, cyclization takes place at a mefa-nitrogen wherever there is an ortho-substituent regardless of the nature of the substituent. This is also found to be true in the case of disubstituted acids (me-k) having one ortho-substituent , where the cyclization takes place at a mefa-nitrogen, yielding 284e-k, respectively. Acids 289a-g in which both orrho-positions are free, thus devoid of any such steric hindrances, are expected on cyclization to give both isomers 290a-g and 291a-g.
Thione 228, on reaction with ethyl chloroacetate and aldehydes, furnishes 230 which is also obtained from 229 and aldehydes (83JIC970) (Scheme 55). No spectral data are cited. ClCH 2CO2Et RCHO I (225) 0 (226) SCHEME 54 $ 0 39 CONDENSED 4-THIAZOLIDINONES Sec. A] (228) (2291 SCHEME 55 (230) 25. Compound 231,on condensation with ethyl chloroacetate and aldehydes in the presence of pyridine and piperidine, yields arylidenethiazolidinone (233) which is also obtained from 232 and aldehydes (83JIC970) (Scheme 56).