Advances in Heterocyclic Chemistry, Vol. 11 by A.R. Katritzky, A.J. Boulton (Eds.)

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 subsequent 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). moreover, R. A. Jones covers the appliance of actual how you can pyrrole chemistry and a truly topical topic, the photochemistry of heterocycles, is reviewed by way 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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Chem. 30, 3427 (1965). Todd, J. Chem. 2102 (1959). 147 L. S. Kaminsky and M. Lamchen, J . Chem. , C 2295 (1966). 42 [SEC. S. T. REID 111. G. 14' \I0 I 0- Prolonged irradiation of nitrones in ethanol, however, leads to the formation of other products, arising presumably from the oxaziridine. 1-oxide (170) and the corresponding Both 2,4,4-trimethyl-l-pyrroline oxaziridine (171) are, for example, converted in this way into 2,4,4trimethyl-1-pyrroline (172) and the N-acetylazetidine (173) ; these products are both believed to arise from the common intermediate 174, formed by cleavage of the nitrogen-oxygen bond of the oxaziridine.

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.

M. Cassal, and C. Sigwalt, Bull. Chim. France 172 T. Sasaki, K. Kanematsu, and A. Kakehi, Chem. Commun. 432 (1969). 948 (1969). 50 S . T. IV. A. A. 1,2-CYCLOADDITION Cycloaddition, analogous in many respects to the dimerization of heterocycles, is frequently observed. '73 Coumarin, on the other hand, undergoes efficient photosensitized addition to tetramethylethylene, cyclopentene, and ketene diethyl acetal 1 7 4 ;the structure of the adduct (205) with ketene diethyl acetal is in agreement with the recent postulate 175 that the geometry of the addition is controlled by an intermediate 7r complex, formed between the excited state of one molecule and the ground state of another.

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