By A. R. Katritzky, A. J. Boulton
During this quantity 3 of the chapters care for particular ring platforms: 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 conceal specific facets of heterocyclic compounds often: cationic cycloaddition reactions (С. К. Bradsher), homolytic fragrant substitution (F. Minisci and nil. Porta), and base-catalyzed hydrogen trade (of ring protons) (J. A. Elvidge, J. R. Jones, zero. O'Brien, E. A. Evans, and H. C. Sheppard).
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Chim. Ital. 97, 289, 304 (1967). g7 G. Bianchetti, P. Ferruti, and D. Pocar, Gazz. Chim. Ital. 97, 579, 597 (1967). g8 A. Lionetti, R. Scarpati, and D. Sica, Gazz. Chim. Ital. 93, 90 (1963). gg R. Huisgen, L. Mobius, and G. Szeimies, Chem. Ber. 98,1138 (1965). looR. Scarpati, M. L. Graziano, and R. Nicolaus, Gazz. Chim. Ital. 99, 1339 (1969). Sec. 1 1,2,3-TRIAZOLES 49 The products are triazolines with the amino or alkoxy function in the 6-position : Addition is regiospecific. I n some cases the triazolines aromatize spontaneously; more usually, aromatization is effected by heating the compounds alone (for enol ether adducts) or with acid or base.
Ugo, ibid. 92, 1040 (1962) ; Chem. Ber. 96, 802 (1963); 0. Bianchetti, P. Dalla Croce, and D. , 97, 1225 (1964); Rend. Ist. Lombard0 Sci. Lettere A , 99, 259 (1965) [Chem. Abstr. 65, 7173 (1966)l; D. Pocar, R. Stradi, and L. M. Rossi, J . Chem. ,Perkin 86, Trans. 1 , 6 1 9 , 769 (1972); Y. K. Kim and M. E. Munk, J . Amer. Chem. SOC. 2213 (1964); M. Regitz and G. Himbert, Ann 734, 70 (1970). Bianchetti, P. Dalla Croce, and D. Pocar, Gazz. Chim. Ital. 94, 340 (1964). 92 P. N. Neuman, J . Heterocycl.
S. Patent 3,324,085; Chem. Abstr. 67, 44802 (1967). 40 S. Maffei and G. F. Bettinetti, Ann. Chim. (Rome)47, 1286 (1957);Chem. Abstr. 52, 7292g (1958). 41 H. Gold, Ann 688, 205 (1965). 42 A. Treibs and K. Jacob,Ann 737, 176 (1970). 43H. G. Adolph, J. Org. Chena. 36, 806 (1971). 34 35 R. H H b Sec. 1 1,2,3-TRIAZOLES 39 3. 27,4 4 * 4 5 Typical conditions involve heating the components a t 150”-170” for 6-20 hours. The products are always 2-trimethylsilyltriazoles, indicating that migration of the trimethylsilyl group from N-1 to N-2 ha5 occurred.