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

By A. R. Katritzky

(from preface)The current quantity comprises 5 chapters, 3 of that are on topics formerly lined 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 prior evaluate of the photochemistry of heterocycles (all via S. T. Reid). which seemed in 1970 in quantity II. Paudler and Sheets have up-to-date their evaluation of the overall chemistry o( naphthyridines, which additionally seemed in quantity II. furthermore, van der Plas. Wo/niak. and van den Haak have in particular thought of the reactions of naphthyridines with nitrogen nueleophiles. principally from their very own large investigations during this area.Hermecv and Mes/aros have surveyed the chemistry of pyrido| l.2-

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REID been proposed to account for the photochemically induced conversion of the sulfoxide (281) to the disulfide (282)231; the ketone group does not, in this case, appear to have any influence on the reactivity. l]non-6-en-2-one (286)233 ; the products are shown in Scheme 23. d Gi,, C0,Me SCHIMI:23 4. Seven-Membered and Larger Heterocycles Relatively few examples of photoreactions of seven-membered and larger heterocycles have been reported. The major products of irradiation of liquid oxepin are hex-5-en-1-01 and h e ~ a n a l photodecomposition ~~~; of cyclic ethers has, in general been shown to be largely dependent on ring size.

Kumar and K . S. Sidhu, /ridimi J . Cheni. 11, 899 (1973). R. C. Petlerson, A. L. Herbert, G. W. Griffin, I . Sarkar, 0. P. Strausz, and J. Font, J . lrrocycl. ('hem. 10, 879 (1973). T. Fujisawa and T. Kobori, Japan Kokai 74142677 [ C A 81, 135999 (1974jl. U. Jacobsson, T. Kempe, and T. Norin, J . OrR, C ' / i w i . 39, 2722 (1974). L. A . -W. Chen, J . A m . CYicvii. Sor. 101, 390(1979j. J . G . Etcifici and C. Diehert, J . Ani. Cliern. Soc. 91, 4595 (1969). J . P. Wosacz, M. M. Joullie, U. Mende, 1.

M . Tokuda, V. V. Chung, A. Suzuki, and M. Itoh, J . Org. C ' / W ~ I ,40, 1858 (1975); V . V. Chung, M. Tokuda, A. Suzuki. and M. Itoh, Bull. Chenr. Soc. Jpn. 49, 341 (1976). V. T. Ramakrishnan a n d J. Kagan. J . C h i . 35, 2898 (1970). Sec. B] OXYGEN- A N D SULFUR-CONTAININGHETEROCYCLES 23 to products 121 and 122, as shown in Scheme 8. l o 2 Ring opening of the oxiran is not stereospecific, and the same two products are obtained on irradiation of the epimeric oxiran. lo3 Me M e Me M e Me (124) 0' (125) Decarbonylation is observed.

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