Advances in Heterocyclic Chemistry, Vol. 33 by A. R. Katritzky

By A. R. Katritzky

(from preface)The current quantity includes 5 chapters, 3 of that are on matters formerly coated in those advances.The photochemistry o( oxygen- and sulfur-containing heterocycles is complementary to the evaluation at the photochemistry oi' nitrogen heterocycles that seemed in quantity 30: jointly those chapters replace an previous evaluation of the photochemistry of heterocycles (all by means of S. T. Reid). which seemed in 1970 in quantity II. Paudler and Sheets have up to date their evaluate of the final chemistry o( naphthyridines, which additionally seemed in quantity II. moreover, van der Plas. Wo/niak. and van den Haak have particularly thought of the reactions of naphthyridines with nitrogen nueleophiles. principally from their very own broad investigations during this area.Hermecv and Mes/aros have surveyed the chemistry of pyrido| l.2-

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161. 835 (1977). ' O h T. Mori, K . H . Yang, K . Kirnoto, and H . Nozaki, Tefral~rdron L e / f . ,2419 (1970) "" A. Padwa, f r r t . J . Su//ur C'lwtn.. Par/ B 7, 331 (1972). "" Io3 24 [Sec. B S . T. ' '' ' 0 (129) 0 ( 130) A wavelength-dependent photoreaction has been described in thecarbonylcontaining thiiran (131)1'3;irradiation at A = 254 nm gave the alkene (132), whereas irradiation at > 280 nm gave products 133 and 134 arising by Type 1 cleavage, followed either by elimination of carbon monoxide or by cyclization to the oxacarbene.

Ory. C'hcw. 35, 1781 (1970). I" K. Muthuramu mid V. Ramamurthy, J . C. S . C ' h m r . , 243 (1980). 12'S. Ito and J. Mori, Bull. Clrrrn. Soc. Jpn. 51, 3403 (1978). 'I5 26 [Sec. B S. T. REID -$ eMe Me Me S ’& Me Me 2. Five-Membered Heterocycles One of the major areas of study in the photochemistry of heterocycles is the photorearrangement of five-membered heteroaromatic systems. Various mechanisms have been proposed to account for these transformations. l Z 3 A ring contraction-ring expansion pathway, via an intermediate cyclopropene, appears to be involved in the rearrangement of derivatives of furan.

Fcrrcr. J. -J. Bonet. H r l c . Chiin. ra 60. 1357 (1977); A. -J. Bonet. ibid. 63, 2390 (1980). J. A . Barltrop. A. C. Day, and C. J. Samuel, J . Ani. ('lzmr. 101. 7521 (1979). ' I x M. Shiozaki and T. Hiraoka. oii Lerr.. 5 (1972); D. H. R. Barton and I-. A . Hulshof, J . C'. S. Perttiti 1. I103 (1977). 'I') N . Ishibe and S. Yutaka. on32. 1331 (1976). ' I o T. Matsuura, T . Takenioto. and R. cihrriron 29, 3337 (1973). P. 0. L. Mack and J . T . Pinhcy, J . C'. S. L'lieiii. C ' m i i i m n , , 451 (1972); R.

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