By A.R. Katritzky, A.J. Boulton (Eds.)
(from preface)Volume 26 includes 3 chapters. C.A.Ramsden experiences heterocy-clic betaines derived from 6-membered heteroaromatic jewelry. 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 just a little ignored team of heterocycles. ultimately, 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. right here back now we have a gaggle of compounds the chemistry of which has complicated significantly over the past decade.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 26
74 N. Dennis, B. Ibrahim, and A. R. s. 105 (1976). 24 CHRISTOPHER A. RAMSDEN [Sec. A \ R R 8 behavior is observed using disubstituted e t h y l e n e ~ The . ~ ~ different orbital symmetry characteristics of 4n-electron I ,3-dipolarophiles results in addition across the betaine 2,4-positions. Compound 123 with 2,3-dimethylbuta-l,3diene gives the 2,4-adduct 128. Cyclopentadiene gives a mixture of products including a 2,4-adduct. 6n-Electron addends are like olefins in that 2,6adducts are formed.
6036 (1965). D. E. Ames, R. F. Chapman, and D. Waite, J . Chem. Soc. C, 470 (1966). D. E. Ames and R. F. Chapman, J . Chem. Soc. C, 40 (1967). D. E. Ames. B. Novitt, D. Waite, and H. Lund, J . Chem. Soc. C , 796 (1969). D. E. Ames and B. Novitt. J. Chem. Soc. C , 2355 (1969). 1 6 4 D. E. Ames, H. R. Ansari, A. D. G. France, A. C. Lovesey, B. Novitt, and R. Simpson, J . Chem. Soc. C, 3088 (1971). 165 D. E. Ames, S. Chandrasekhar. and R. Simpson, J . C . , Perkin 1, 2035 (1975). 1 6 6 G . M. Singerman, in “The Chemistry of Heterocyclic Compounds” (R.
B CHRISTOPHER A. RAMSDEN The 2-alkylcinnolinium-4-olates (233) are stable, colorless compounds. , 234; R' = M e and 246); this trend is useful for diagnosing the position of alkylation of 4-hydroxycinnolines. " O S 1 '' The chemical reactions of the cinnolinium-4-olates (233) are conveniently illustrated by considering specific reactions of the 2-methyl derivative (243) (Scheme 10). Compound 243 readily forms salts: Ethanolic hydrogen chloride gives 2-methyl-4-hydroxycinnolinium chloride (239)' 5 4 and triethyloxonium tetrafluoroborate gives 2-methyl-4-ethoxycinnolinium tetra- &+ OEt 0- I BF; \ NGNMe W N M e (239) // \ a: 0 v ' S I @+ \ vi N' 0 II N//NMe C0,Me SCHEME 10.