Advances in Heterocyclic Chemistry, Vol. 49 by Alan R. Katritzky (Ed.) 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 college of Ljubljana, Yugoslavia hide the development in pyridazine chemistry considering 1979, the date in their prior ebook in quantity 24 of Advances.Professor Vorbruggen of Berlin has contributed a survey of the amination of nitrogen heterocycles, which bargains relatively with aminations within which an ami no crew replaces another performance at the heterocyclic ring. hence, this overview 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. ultimately, Professor T. A. Crabb of Portsmouth, England has coated 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 prior to.

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Extra resources for Advances in Heterocyclic Chemistry, Vol. 49

Example text

210 reacts with ethyl a-haloproand oxalyl chloride to afford pionate, ethyl 2-chloro-3-anilinocrotonate, 211b and 212a,b, respectively (84M13)(Scheme 49). R=H b , R =CH$CH2)3 SCHEME48 36 HRUSHl K. PUJARl (2121 [Sec. l l . A (210 1 a , X=C(Me)NHPh b, X=O (211 ) 0 ,R - H b , RZMe SCHEME 49 19. Thiazolo[3,2-a]-[l,3]diazocin-3(2H)-ones Dehuri and Nayak (83JIC970) reported that 3,4,5,6,7,8-hexahydro1,3-diazocine-2-thione (213), obtained from I ,5-dibromopentane and thiourea in boiling ethanol, reacts with chloroacetic acid or its ethyl ester followed by basification to give 5H-6,7,8,9-tetrahydrothiazolo[3,2-a][ 1,3]diazocin-3(2H)-one(214).

Coffen and co-workers have also reported that benzodiazepine containing a sulfide bridge (196), obtained by the reaction of 193 with hydrogen sulfide, reacts with mercaptoacetic acid in tetrahydrofuran to furnish only the monolactam 194 (75USP3850948; 76USP3906001). However, with I ,4-benzodiazepinone as a substrate, a much longer reaction time was needed. 4-benzodiazepin-2-one (197), on refluxing with mercaptoacetic acid in benzene for five days, furnished the desired condensed thiazolidinone (198) (74JOC 167).

The reaction of 247 with DMAD in methanol results in the exclusive formation of thiazinone 24. The reaction can be catalyzed by sodium methoxide. In the absence of added base, thiazolidinone 23 is formed in addition to compound 24. This is in contrast to the findings in the reactions of thioureas with DMAD in which thiazolidinones are the only isolable products. the enhanced stability of the 6,5,6-ring system because of pseudoaromaticity and to the inherent strain present in the 6,5,5-ring system, or it may be due to the difference in basicity between a benzimidazol yl-2-thione and thioureas.

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


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