By Alan R. Katritzky (Ed.)
ISBN-10: 0120206498
ISBN-13: 9780120206490
(from preface)Volume forty nine of Advances in Heterocyclic Chemistry includes 5 chapters. Professors M. Tiller and B. Stanovnik of the collage of Ljubljana, Yugoslavia disguise the growth in pyridazine chemistry in view that 1979, the date in their earlier booklet in quantity 24 of Advances.Professor Vorbruggen of Berlin has contributed a survey of the amination of nitrogen heterocycles, which offers rather with aminations during which an ami no workforce replaces another performance at the heterocyclic ring. therefore, this evaluate enhances our contemporary assessment in quantity forty four facing the Tschitschibabin response, during 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 take care of bicyclic heterocycles. Dr. H. ok. 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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Example text
Thiazolobenzodiazepinones All four possible structural isomers of thiazolobenzodiazepinones, namely, thiazolo[ I ,3]benzodiazepinone, thiazolo[ I ,4]benzodiazepinone, thiazolo[ I ,5]benzodiazepinone, and t hiazolo[2,4]benzodiazepinone have been synthesized. a. Thiuzolu[2,3-b]-[1,3]henzodiuzepin-3(2H)-ones. 4,5-Dihydro-5methyl- I ,3-benzodiazepine-2-thione(190)reacts with ethyl chloroacetate and ethyl a-bromo-n-hexanoate to give 5,6-dihydro-6-methylthiazolo[2,3b]-[I ,3]benzodiazepin-3(2H)-one(191a)and its 2-n-butyl analog (191b);the latter is isolated as its hydrochloride (69JHC491).
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).
2-Hydrdzino-4-thiazolidinone (146, R = H) reacts with chloroacetic anhydride to afford 147 which, on pyrrolysis, readily cyclizes to give 2H,7H-5,6-dihydrothiazoIo[2,3-c]-[I ,2,4]-triazin-3,6-dione (148) (72ZOR1722). Reaction of phenyl derivative 146 (R = Ph) with ethyl bromoacetate gives cyclized prodI ,2,4]-triazin-3,5-dione uct 2H,7H-7-phenyl-5,6-dihydrothiazolo[2,3-c]-[ (149) (84MI2) (Scheme 32). 4]-triazin-3(2H)-one(151, R = Me, R' = H) (70JHC123I ). Similarly, 150 ( R = Me) reacts with a-cyanobenzyl p-toluene sulfonate [PhCH(CN)OTS] or a-cyanobenzyl bromide I PhCH(CN)Br]to afford 151 (R = Me, R' = Ph) (71JHC621).
Advances in Heterocyclic Chemistry, Vol. 49 by Alan R. Katritzky (Ed.)
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