By A.R. Katritzky, A.J. Boulton (Eds.)
(from preface)This, the 11th quantity of Advances in Heterocyclic Chemistry, comprises surveys of the chemistry of the next teams of heterocyclic compounds: benzothiophenes (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 tips on how to pyrrole chemistry and a truly topical topic, the photochemistry of heterocycles, is reviewed via S. T. Reid.Suggestions are welcomed for contributions to destiny volumes; they need to be within the kind 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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Extra info for Advances in Heterocyclic Chemistry, Vol. 11
88, 1844 (1966). D. W. Kurtz and H. Shechter, Chern. Cornmun. 689 (1966). 138 H. Goth, A. R. Gagneux, C. H. Eugster, and H. Schmid, Helv. Chim. Acta 136 137 139 50, 137 (1967). E. E. van Tamelen and T. H. Whitesides, J . Am. 90,3894 (1968). F’. S. T. 140Ring cleavage also occurs in 1,2,5-oxadiazoles, 1,2,5-thiadiazoles, and 2 H - l , 2 , 3 - t r i a z o l e ~ . ~ ~ ~ 0 Ph FK “0 (155) NH2 hv Ph __j ether I + Ph-C=N-CO-Ph (156) (157) Photorearrangement has been observed in certain pyrazoles. 1421,4,5-Trimethylimidazole (160) itself undergoes rearrangement t o the alternative 1,2,5-trimethylimidazole ( 161),143presumably by a different pathway.
40, 882 (1962). 126 P. Beak and J. L. Miesel, J . Am. Chem. 89, 2375 (1967). 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.
63 I n benzene, (73) (75) Ph ROH ___t I RO--C-CO-NH-N=C I Ph /Ph kPh (74) diphenylketene and diphenyldiazomethane are reversibly formed, whereas in an alcohol, solvent incorporation occurs and the product has the structure 74. 63 The N-methylisoxazolidine (76) undergoes ring expansion to the tetrahydro-1,3-oxazine (77) on photolysis in hexane 6 4 ; the rearrangement can be accounted for in terms of an initial nitrogenoxygen bond cleavage, followed by hydrogen transfer from the methyl group t o the nitrogen atom and subsequent carbon-oxygen bond formation.