Read e-book online Advances in Heterocyclic Chemistry, Vol. 49 PDF

By Alan R. Katritzky (Ed.)

ISBN-10: 0120206498

ISBN-13: 9780120206490

(from preface)Volume forty nine of Advances in Heterocyclic Chemistry comprises 5 chapters. Professors M. Tiller and B. Stanovnik of the collage of Ljubljana, Yugoslavia conceal the growth in pyridazine chemistry when you consider 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 bargains rather with aminations within which an ami no workforce replaces another performance at the heterocyclic ring. hence, this assessment enhances our fresh overview in quantity forty four facing the Tschitschibabin response, during 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. ok. Pujari of Kurukshetra college 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 structures 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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3-6]-[I ,3]benzodiazocin-3(2H)-one (217) was assigned without any evidence (77M13) (Scheme 5 1). The cyclized product could also be represented by the alternate structure 218. 3]diazonin-3(2H)-one (220). The thiazolidinone (220) is also obtained, albeit, in low yield by heating thione 219 and ethyl chloroacetate, followed by basification. Compound 219, on reaction with ethyl chloroacetate and aromatic aldehydes in the presence of pyridine and piperidine, furnishes directly the arylidene thiazolidinone 221 which is also obtained by condensation of 220 with aldehydes (83JIC970) (Scheme 52).

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). The structural assignment for cyclized product 191 was based on 'H-NMR spectral data; the product did not show a large downfield shift of an aromatic proton (HA) which rules out the other alternate structures 192.

249a and 252, respectively, as reported by Russian workers (60MII; 61UKZ503)(Scheme 61). The thione 247 reacts with chloroacetic acid and aldehydes in a mixture of acetic acid and acetic anhydride to give arylidene thiazolidinone (253) [86IJC(B)776] which can also be obtained by the reaction of aldehydes 72M11)or with thiazolidinone 249a with acid 248 (R = R' = H) (56JOC24; (56JCS361). Likewise, thiones 254a-d react with chloroacetic acid; subsequent heating of the intermediate acids 255a-d with acetic anhydride in pyridine SCHEME 61 HKUSHI K.

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


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