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: 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 appliance of actual ways 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 because of the Editorial Board, the writer, and the authors for his or her cooperation.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 11
460. W h y , New York, 1966. 111. 130 Ring cleavage also occurs in pyridine, but the photochemical step in this case appears to be the photosensitized addition of water to pyridine, rather than direct carbon-nitrogen bond cleavage; an acyclic product is formed when the photolysis is carried out in basic solution [Eq. 131 Of greater interest, however, is the extent to which the photochemistry of a heteroaromatic system parallels that of benzene and its derivatives. Pyrazine (143 ; R = H) and 2-methylpyrazine (143 ; R = CH3) undergo photoisomerization both in the vapor phase and in solution with light of 253 nm wavelength to yield pyrimidine (144; R 1 = R 2 = R 3 = H ) ,and a mixture of 4-methyl- (144; R1=CH3, R 2 = R 3 = H ) ,5-methyl- (144; R 2 = C H 3R1 = R 3 = H ) ,and probably 2-methyl-pyrimidine (144; R3= CH,, R1 = R 2= H), r e s p e c t i ~ e 1 y .
A similar effect is observed in the photolysis of 5,5-dimethyl-l-pyrroline 1- 0 ~ i d e . to the emide (X78) and an intermediate oxaziridine may -be involved in the photochemical of aryl oximes into the corresponding amides [Eq. (42)]. The heteroaromatic N-oxides have been the subject of more recent investigation. The structure of the photoproduct appears to be dependent on a number of factors including the nature of the heterocycle and its substituents, and the solvent employed in the photolysis.
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.