By A.R. Katritzky, A.J. Boulton (Eds.)
(from preface)This, the 11th quantity of Advances in Heterocyclic Chemistry, contains surveys of the chemistry of the subsequent 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). additionally, R. A. Jones covers the applying of actual how 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 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 resources for Advances in Heterocyclic Chemistry, Vol. 11
180 J. 181 G. IV. A. S. T. lss The same transformation has been observed in norbornadiene, and other intramolecular cycloadditions are known [see, for example, Eq. (50) ls7]. An intermediate of this type has been postulated ls8 to account for the photorearrangement of 1,4-epoxy1,4-dihydronaphthalene to benz[f]oxepin [Eq. (51)]. hv. l~~ The two major products are the 1,4-dimer and the pentacyclic derivative (213), arising presumably by intramolecular photocycloaddition 186 E. Payo, L. Cortb, J. Mantecbn, C.
89,4805 (1967). 97 W. Kirmse and L. Horner, Ann. C h m . 614, 4 (1958). P. 30 S. T. REID [SEC. 111. E. products is rationalized in terms of a diradical intermediateg7[Eq. (27)]. 98 Ph hv Ph hv __f E. HETEROCYCLIC DIENES One of the many photoreactions of conjugated dienes is the formation of cyclobutenes,99and this has been reported both in cyclic and acyclic dienes. lOO This photoreaction is frequently observed in heterocyclic systems. A number of azacycloheptadienes are photochemically isomerized, in an identical manner to cycloheptadiene itself, to bicyclic derivatives.
H. Issidorides, Tetrahedron Letters 753 (1967). and C . Sigwalt, Tetrahedron Letters 1347 (1966). A. Alkaitis and M. Calvin, Chem. Commun. 292 (1968). 160 M. Ogata and K. Kano, Chem. Commun. 1176 (1967). 158 J. Streith 159 S. T. REID 46 [SEC. 111. G. R = H, CHI (43) Heteroaromatic N-oxides are also frequently observed to undergo ring expansion with the formation of oxazepines. Photolyses in or acetone 162 of a series of 2-substituted quinoline benzene 1-oxides yield, as the principal product, the substituted benz[d]-1,3oxazepine ;for example, both 2-phenylquinoline 1-oxide and 2-cyanoquinoline 1-oxide are converted into the corresponding oxazepine [Eq.
Advances in Heterocyclic Chemistry, Vol. 11 by A.R. Katritzky, A.J. Boulton (Eds.)