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 growth in pyridazine chemistry considering 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 quite with aminations during which an ami no team replaces another performance at the heterocyclic ring. hence, this overview enhances our contemporary overview 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 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 ahead of.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 49
From u Thiuzok. There are only two instances that describe the synthesis of thiazolo[3,2-a]pyrimidin-3(2H)-ones through this route. 5 3 Dimethyl-2-imino-4-thiazolidinone (132)reacts with alkylmalonyl chloride to give the acids 133 which, on pyrrolytic dehydration, furnish 2,2-dimethyl-6-alkyl-4,5,6,7- tetrahydro-2H- thiazolo[3,2-a]pyrimidin-3,5,7triones (134) (5OJCSl 127). A better result is obtained by heating the acid in a vacuum. Similarly, the bicyclic compound 137 is prepared by reacting 5-arylidene-2-imino-4-thiazolidinones (135) with ethyl acrylate and then cyclizing the resulting intermediate esters 136 with acetic anhydride (75IJC238) (Scheme 29).
Reaction of 4,5-dihydro-5,6-diphenyl1,2,4-triazine-3-thione (164)with chloroacetic acid gave a product for which structure 167 was assigned by Ali et al. (75IJC109) by analogy with the work on 168 of Bogachev and Fomenko (66URP175968) and also of Trepanier and Kreiger on 151 (70JHC1231). Later, 167 was modified to 6,7-diphenyl-7H-thiazolo[3,2b]-[1,2,4]-triazin-3(2H)-one(165)[77IJC(B)46]. Unfortunately, Ali and co- SCHEME35 28 HRUSHI K. PUJARI [Sec. A workers (75IJC109) are not justified in citing the structural analogy of the Russian workers (66URP175968) whose work itself lacks supporting evidence.
Compound 150, however, on reaction with I ,2-dibromoethane, furnished another bicyclic system (154). The difference in the behavior of 150 toward dibromoethane and other reagents such as ethyl bromoacetate and a-cyanobenzyl p-toluene (1L 6 1 (147 1 R= H R= Ph SCHEME 32 26 HRUSHI K. PUJARI [Sec. A sulfonate is due to the presence of an sp3-functionalized carbon in the former and an sp2-functionalized carbon in the latter (71JHC621)(Scheme 33). ii. Thiazulu[3,2-b]-[i,2,4]-triazin-3(2H)-ones. Reaction of 6-methyl-Soxo-l,2,4-triazine-3-thione (155,R = Me) with bromoacetic acid in the presence of metallic sodium in ethanol gave a product, 2H,7H-6methylthiazolo[3,2-b]-[ 1,2,4]-triazin-3,7-dione, for which structure 157 was assigned (68ACH191).