By A. R. Katritzky, A. J. Boulton
During this quantity 3 of the chapters take care of 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 additional chapters hide specific facets of heterocyclic compounds mostly: cationic cycloaddition reactions (С. К. Bradsher), homolytic fragrant substitution (F. Minisci and zero. 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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Extra info for Advances in Heterocyclic Chemistry, Vol. 16
T. L. GILCHRIST AND 0 . E. eaThe triazoline adducts of the enamine tautomers are aromatized by treating with acid, and in these conditions the triazoline appears to undergo a Dimroth rearrangement before elimination of the amine, because two triazoles are obtained, one of which has H x T > N Y RNH __+ ZX) 11';. R' + R' N R SCKEME 16 the imine nitrogen in the ring (Scheme 16). l o l 4. From Axides and OleJins with Electron-Withdrawing Substituents Olefins, RCH=CHX, with a strongly electron-withdrawing substituent X (CN,NOz, C1, F, SOzCl)react with organic azides to give triazolines of varying stability; from these a stable fragment can be eliminated to give triazoles.
Abetr. 68, 87243 (1968)l. 65 G. S. Akimova, V. N. Chistokletov, and A. A. Petrov, Zh. Org. Khina. 1, 2077 (1965) [Chem. Abstr. 64, 9713 (1966)l; ibid. 3, 968 (1967) [Chem. Abstr. 67, 100071 (1967)l; ibid. 4, 389 (1968) [Chem. Abstr. 68, 105100 (1968)l. 66 E. Robson, J. M. Tedder, and B. Webster, J . Chem. , 1863 (1963). 68 42 T. L. GILCHRIST AND G . E. GYMER [Sec. B. RM"H* RIN\ 4 N N I H+ R'N, 6N N SCHEME 4 B. FROM AZIDESAND ACTIVATED METHYLENECOMPOUNDS The base-catalyzed condensation of azides with activated methylene compounds is a well-established route to 1H-triazoles.
Dornoa and H. Hell, Hell, Chem. Ber. Ber. 93, 93, 1998 1998 (1960). (1960). 73 74 H. Bojarska-Dahlig, Rec. Trav. Chim. 80, 80, 1348 1348 (1961). (1961). 74 75 G. G. L’abb6 L’abb6 and A. A. Hassner, J. Heterocycl. Heterocycl. Chem. Chem. 7, 7, 361 361 (1970). (1970). 75 76 D. R. Sutherland Sutherland and G. G. Tennant, Tennant, JJ .. Chem. SOC. SOC. C,, 706 706 (1971). (1971). 76 C Sutherland and G. Tennant, Tennant, J. Chem. Chem. SOC. SOC. C,, 2156 2156 (1971). (1971). 77 D. R. Sutherland C YY tcF I+ H H H WW Sec.
Advances in Heterocyclic Chemistry, Vol. 16 by A. R. Katritzky, A. J. Boulton