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 jewelry. those compounds were intensively studied during the last 10 years and feature no longer formerly been comprehensively reviewed. O. Meth-Cohn and B. Tarnowski summarize the chemistry of the thiocoumarins, a a bit ignored team 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 now have a gaggle of compounds the chemistry of which has complicated significantly over the past decade.
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In addition to the endo dimer (136; R = Me) (7573, the 5-methyl derivative (132; R = Me) also gave a small amount of the exo dimer (135; R = Me) (673. The dimerization (132 --t 136) appears to be rapid and irreversible: Attempts to trap the betaines (132)using 1,3-dipolarophiIes in situ were not successful. It is notable that whereas the isoconjugate pyridinium-3-olates (86) (Section 111,A,2)form exo dimers (Scheme 3), the thiopyrylium-3-olates (132) favor endo dimers. 75a 5 , Py r idazin ium-3-o la tes (137) (137) 75a (138) S.
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O' 5 . '05 Subsequently, this product has been prepared by treatment of the iodide 190 with potassium carbonate, and the betaine structure has been confirmed by spectroscopic and chemical studies. Compound 189 (R' = Me, R2= R3 = H) is isolated as hydrated violet-red needles. ' 0 6 , ' 0 7 Bromination gives the 5,7-dibromo derivative (189; R' = Me, R2= R3= Br), which is also obtained from 5,7-dibromo-8-hydroxyquinoline and diazomethane. ' O7 6. 2-Benzothiopyrylium-4-olates(191) lo4 lo' Io6 lo' G.