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

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

(from preface)Volume 26 comprises 3 chapters. C.A.Ramsden experiences 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 little ignored workforce 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 we have now a gaggle of compounds the chemistry of which has complex significantly over the past decade.

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Org. C k m . 41, 1570 (1976) 48 CHRISTOPHER A. RAMSDEN [Sec. B hydrazones (263) gives the explosive N-oxides 262 which are reduced -'~~ to betaines 261 in good yield by stannous ~ h l o r i d e . ' ~ ~Alternatively, these compounds (261)can be prepared, also in good yield, by N-alkylation (R2s04)'89-1 or N-arylation (Ar21+C1-)'89 of 1,2,3-benzotriazin-4(3H)one (264). '85-'89Structures 261 and 262 were first recognized by Kerber'" in 1972 and confirmed in 1974 by McKillop and K ~ b y l e c k i " ~who have also summarized the conclusions of earlier structural investigations.

76 77 Sec. 83,84 The mechanism of this photoisomerization is not clear; similar rearrangements of mesoionic rings have been observed' (see also Section III,D,l). 1 H O C H y y O H \0 ' I1 COzH NHR (147) (148) (149) SCHEME 6 . Reagents: i, R N H N H , : ii. AT, H + / H , O ; iii. hv. B. SYSTEMS WITH ELEVEN CONJUGATED ATOMS 1. 2-Benzopyrylium-4-olates (150) 0 &R \ 2 /o+ R' (150) C0,Me C0,Me Y . Maki, M. Suzuki, T. Furuta, T. Hiramitsu, and M. , 4107 (1974). 8 4 Y. Maki and K. ), Japanese Patent 75 101,369 [CA 84, 59532 (1976)l.

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,. 71Intramolecular reaction (120 -+ 121) is slow: In the N.

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