By A. R. Katritzky, A. J. Boulton
During this quantity 3 of the chapters care for particular ring structures: 1,2,3-triazoles (T. L. Gilchrist and G. E. Gymer), dibenzothiophenes (J. Ashby and С. С Cook), and the 7-azabicyclo[2.2.1]heptadienes, and their diminished, and benzo-fused, derivatives (L. J. Kricka and J. M. Vernon). 3 extra chapters hide specific facets of heterocyclic compounds quite often: cationic cycloaddition reactions (С. К. Bradsher), homolytic fragrant substitution (F. Minisci and zero. Porta), and base-catalyzed hydrogen alternate (of ring protons) (J. A. Elvidge, J. R. Jones, zero. O'Brien, E. A. Evans, and H. C. Sheppard).
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During this quantity 3 of the chapters care for particular ring structures: 1,2,3-triazoles (T. L. Gilchrist and G. E. Gymer), dibenzothiophenes (J. Ashby and С. С Cook), and the 7-azabicyclo[2. 2. 1]heptadienes, and their decreased, and benzo-fused, derivatives (L. J. Kricka and J. M. Vernon). 3 additional chapters hide specific points of heterocyclic compounds regularly: cationic cycloaddition reactions (С.
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 16
Example text
Chem. 35, 2027 (1970); D. Seyferth and P. Hilbert, Org. Prep. Proced. Int. 3 , 51 (1971). 20 R. Buijle, R. Fuks, and H. G. Viehe, Angew. Chem. Int. Ed. Engl. 5 , 5 8 5 (1966). 2Oa P. Ykman, G . L'abbB, and G. Smets, Chem. Ind. (London),886 (1972). 2 1 E. Fabbri, P. Vita Finzi, and P. Grunanger, Gazz. Chim. Ital. 90, 413 (1960). VitaFinziandC. Scotti, AttiAccad. Naz. , Mat. Nut. 41, 204 (1966) ; Chem. Abstr. 67, 54080 (1967). 2 3 R. E. Harmon, R . A. Earl, and S . K. Gupta, Chem. Commun. 296 (1971).
Biophys. Acta 213, 288 (1970). 86 R. N. Maslova, E. A. Lesnick, and Ya. M. Varshavsky, Biochem. Biophys. Rea. Commun. 34, 260 (1969). 82 This Page Intentionally Left Blank I ,2,3-Triazoles T. L. GILCHRIST AND (3. E. GYMER The Robert Robinson Laboratories, University of Liverpool, Liverpool, England I. Introduction . 11. Synthesis of the Triazole Ring . A. From Azides and Acetylenes . B. From Azides and Activated Methylene Compounds C. Other Routes Involving Azides . D. 1H-Triazoles from a-Diketone Derivatives .
GYMER The toluene-p-sulfonamido anion may be lost from this, giving the diazo compound directly, or ring closure (which may be reversible) can take place, giving the triazoline anion (2). I n many of these cases it is impossible to decide, without 15N-labeling experiments, whether the third nitrogen of the triazole ring is derived from the toluene-p-sulfonyl azide or from the activated methylene compound. ^^ Two moles of azide are required, the second being reduced to aniline. No mechanism has been proposed for the reaction; 81 M.