By A.R. Katritzky, A.J. Boulton (Eds.)
(from preface)Volume 26 includes 3 chapters. C.A.Ramsden reports heterocy-clic betaines derived from 6-membered heteroaromatic earrings. those compounds were intensively studied over 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 slightly overlooked crew of heterocycles. ultimately, W. Friedrichsen has reviewed the chemistry of the benzo[r]furans which, in contrast to the aza and thia analogs, haven't formerly been thought of during this sequence. the following back now we have a gaggle of compounds the chemistry of which has complicated significantly during the last decade.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 26
In most of these cycloaddition reactions the energy of the HOMO is the controlling factor. , 124 and 125; R = CO,Me, CN, COMe). With styrenes the endo isomer (126) predominates. These adducts (126) are transformed into isomers 127 by trifluoromethanesulfonic acid. 74 Ethyl vinyl ether gives exclusively the endo adduct (124; R = OEt). Similar ooI R H NO2 ( 123) (124) (125) " J . Banerji. N . Dennis, J. Frank, A. R. Katritzky, and T. Matsuo, J . C . , Perkin I, 2334 (1976). 7 3 N . Dennis, B. Ibrahim, and A .
Ullman and W. A. Henderson, J . Am. Chem. Soc 88, 4942 (1966). 90 H. E. Zimmerman and R. D. , 1847 (1964). K. Undheim and B. P. Nilsen, Acra Chem. , Ser. B 29, 503 (1975). 9 2 J. W. Lown and K. Matsumoto, Can. J . Chem. 49, 3443 (1971). 85 86 Sec. B] 29 HETEROCYCLIC BETAINES is also formed from the betaine 150 (R’ = R 2 = Ph) and diphenylacetylene. 92 Prolonged thermolysis of compound 151 (R’ = R2 = Ph) results in the formation of a pair of dimeric products which have been formulated as compounds 160 (47%) and 161 (4%) and which can be regarded as being formed by addition of the indenone carbonyl group to the betaine.
Evidence for this steric effect is provided by observation that, when using bulky alkyl groups, or with 8-substituted-4-hydroxycinnolines,almost exclusive formation of the mesomeric betaine (233) O C C U ~ S In. , rnethyl,l6' b r ~ m o , ' ~pheny1,'62,'67 ~ alkylcarboxy,' 5 7 , 1 6 8 CH,CO,R' 59) leads to predominance of the l-alkylcinnolin4-one (234) which is sometimes the only product. '61 Methylation of 4hydroxy-6-bromo-3-cinnolinecarboxylicacid at room temperature (Me,S04/aq KOH) gives equal amounts of the inner salt 236 and the I-methyl isomer (234; R' =Me, RZ=CO,H, R3= R 5= R6 = H, R4= Br): Compound 236 is decarboxylated in hot dimethylformamide giving the mesomeric betaine (233; R' = Me, R2 = R3 = R5= R6 = H, R4 = Br).
Advances in Heterocyclic Chemistry, Vol. 26 by A.R. Katritzky, A.J. Boulton (Eds.)