Download e-book for kindle: Advances in Heterocyclic Chemistry, Vol. 11 by A.R. Katritzky, A.J. Boulton (Eds.)

By A.R. Katritzky, A.J. Boulton (Eds.)

ISBN-10: 0120206110

ISBN-13: 9780120206117

(from preface)This, the 11th quantity of Advances in Heterocyclic Chemistry, contains surveys of the chemistry of the next teams of heterocyclic compounds: benzo[6]thiophenes (B. Iddon and R. M. Scrow-ston), naphthyridines (W. W. Paudler and T. J. Kress), and quinu-clidines (L. N. Yakhontov). furthermore, R. A. Jones covers the applying of actual the way to pyrrole chemistry and a really topical topic, the photochemistry of heterocycles, is reviewed by means of S. T. Reid.Suggestions are welcomed for contributions to destiny volumes; they need to be within the type of brief sj'nopses.Thanks are as a result of the Editorial Board, the writer, and the authors for his or her cooperation.

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F. Semmelhack, R. B. Hornby, and J. C. Vederas, Chem. Commun. 686 (1968). 122 123 T. SEC. 111. lZ6Other photochemical rearrangements are FeC14- phQ-cHs Ph Ph Ph (136) (135) Ph (137) also best interpreted as arising via an initial ringe cleavage. In this way, the conversion of 2,3-dihydro-5,6-dimethylpyrazineinto 1,4,5trimethylimidazole in 70% yield by photolysis in ethanol probably involves the intermediate diimine which undergoes rapid cyclization to the imidazole [Eq. F. Durst, Can. J . Cfiern.

111. F. S. T. REID enlargement and 2,3-diphenyl-6,7,8,g-tetrahydro-BH-imidazo[1,2-u]azepine (139) is obtained. l~~ This is believed to be the result of an initial disproportionation reaction yielding hexahydroand tetrahydro-2,4,6-triphenyl-s-triazine. ”YN+ Ph “YN Ph (140) L’”Z ph)(Nyph H Ph Ph (141) + ”Y” Ph (142) F. HETEROAROMATIC SYSTEMS A number of reports of photochemical decomposition of heteroaromatic compounds have appeared in the literature during the past 50 or 60 years. A few of these undoubtedly involve photooxidative processes, whereas others have been examined in the vapor phase, often a t elevated temperatures.

667 (1966). T. Janjiki, H. Kato, and M. Ohta, Chem. Commun. 496 (1968). 78 P. Dowd, J . Am. Chem. SOC. 88, 2587 (1966). 7 9 C. G. Overberger and C. Yaroslavsky, Tetrahedron Letters 4395 (1965). ] THE PHOTOCHEMISTRY OF HETEROCYCLES 25 trans-1,5-diphenylpent-l-ene. 80 O-CO-CZHB “Y P h q P ‘h/ N=N Ph HPh A similar type of photoinduced ring cleavage is reported for diazirines, which have mostly been studied in the gas phase. Diazirine itself in the presence of nitrogen or a hydrocarbon is decomposed to methylene and nitrogen [Eq.

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