By A.R. Katritzky, A.J. Boulton (Eds.)

ISBN-10: 0120206269

ISBN-13: 9780120206261

(from preface)Volume 26 comprises 3 chapters. C.A.Ramsden reports heterocy-clic betaines derived from 6-membered heteroaromatic earrings. those compounds were intensively studied during the last 10 years and feature now not formerly been comprehensively reviewed. O. Meth-Cohn and B. Tarnowski summarize the chemistry of the thiocoumarins, a a bit of overlooked staff of heterocycles. eventually, W. Friedrichsen has reviewed the chemistry of the benzo[r]furans which, not like the aza and thia analogs, haven't formerly been thought of during this sequence. the following back we have now a gaggle of compounds the chemistry of which has complex significantly during the last decade.

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Cbeni. , 770 (1975). N. Dennis, A. R . Katritzky, and H . Wilde, J. C . , Ptrkin I , 2338 (1976). 62 J . Banerji, N. Dennis, A. R. Katritzky. R. L. Harlow. and S . H. Simonsen. J . Cbem. Res. 38 (1977); J. Cbrni. R P . 517 (1977). 6 3 T. Lierum and K. Undheim. Actu Cbetn. S c u d . , Ser. -0. Ranger, G . A. Ulsaker, and K. ,70. 64 A. Mori, S. Ohta, and H. Takeshita. Heterocycles 2,243 (1974); H. Takeshita, A. Mori, and S. Ohta, Bull. Cbem. Soc. Jpn. 47, 2437 (1974). 6 5 A. R. Katritzky and Y .

Typically, acrylonitrile gives compound 181 (R = C6H11, R' = R3 = R4 = H, R' = CN). Other olefinic 1,3-dipolarophiles that have been used are N-phenylmaleimide, dimethyl fumarate, cyclohexene, norbornene, and norbornadiene. The exclusive formation of endo adducts (181; R' = R3 = H) may be due to the bulky N-substituent. In a similar manner acetylenes give 1,3-dipolar cycloadducts : dimethyl acetylenedicarboxylate gives 182 (R = C6Hll, R' = RZ = C0,Me); methyl propiolate gives mainly 182 (R = C,Hll, R1 = H, R' = C0,Me); methyl phenylpropiolate gives a mixture of stereoisomeric adducts (182; R = C6H, 1, R' = C0,Me or Ph, R' = Ph or C0,Me); and benzyne gives compound 183.

Takeshita. Heterocycles 2,243 (1974); H. Takeshita, A. Mori, and S. Ohta, Bull. Cbem. Soc. Jpn. 47, 2437 (1974). 6 5 A. R. Katritzky and Y . Takeuchi, J . A m . Chem. Soc. 4134 (1970). 66 A. R. Katritzky and Y. Takeuchi, J. Cheni. Soc. c', 878 (1971). 67 N. Dennis, A. R. Katritzky, S. K. Parton. Y . Nomura, Y. Takahashi, and Y . Takeuchi, J . C . , Perkin I , 2289 (1976). 6o 61 22 CHRISTOPHER A. RAMSDEN [Sec. 69 Iiii (113) SCHEME5. Reagents: i, RC-CH; (114) (115) ii, RCH=CH,; iii, MeI; iv, Ag,O or NaHCO,.

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Advances in Heterocyclic Chemistry, Vol. 26 by A.R. Katritzky, A.J. Boulton (Eds.)

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