The synthetic usefulness of a new method of 1,2,3-triazole synthesis has been demonstrated. By employing cyclic enamino esters 3 and enamino ketones 4 in reactions with 5,7-dinitro-3-diazo-1,3-dihydro-2H-indol-2-one (1), bicyclic triazoles 5 and 6 have been prepared in good to excellent yields. © 1994.502367236726Augusti, Kascheres, (1993) J. Org. Chem., 58, p. 7079Greenhill, Enaminones (1990) Chemical Society Reviews, 6, p. 277Sainsbury, (1984) Rodd's Chemistry of Carbon Compounds, 4 (500). , M.F. Ansell, Elsevier, New York (NY), Chapter 18Wamhoff, (1984) Comprehensive Heterocyclic Chemistry, 5, p. 669. , K.T. Potts, Pergamon Press, OxfordGrundmann, Haldenwanger, Über die Gefahren beim Umgang mit Methylazid (1950) Angewandte Chemie, 62, p. 410Katritzky, Lagowski, (1984) Comprehensive Heterocyclic Chemistry, 5, p. 39. , For example, 1,2,3-triazoles are much less reactive than pyrroles in electrophilic aromatic substitution, see:, K.T. Potts, Pergamon Press, OxfordAnderson, McPherson, New, Rick, (1984) J. Med. Chem., 27, p. 1321Anderson, Bhattacharjee, Houston, (1989) J. Med. Chem., 32, p. 119Anderson, Corey, (1977) J. Med. Chem., 20, p. 812Mattocks, Pyrrolizidine alkaloid analogues. Part 2. Further hydroxymethyl-1-methyl-3-pyrrolines (synthanecines), and the preparation and esterification of some hydroxymethylpyrroles (1978) Journal of the Chemical Society, Perkin Transactions 1, p. 896Ladurée, Lancelot, Robba, Chenu, Mathé, Synthesis and evaluation of antileukemic activity of 5-thienyl- or 5-(2-furyl)-2,3-dihydro-6,7-bis(hydroxymethyl)-1H-pyrrolizine bis(alkylcarbamates) and derivatives (1989) Journal of Medicinal Chemistry, 32, p. 456Anderson, Chang, McPherson, (1983) J. Med. Chem., 26, p. 1333Barbour, Robins, Pyrrolizidine alkaloid analogues. Synthesis of 11-membered macrocyclic diesters of (�)-synthanecine A (1985) Journal of the Chemical Society, Perkin Transactions 1, p. 2475Zalkow, Glinski, Gelbaum, Moore, Melder, Powis, Semisynthetic pyrrolizidine alkaloid N-oxide antitumor agents. Esters of heliotridine (1985) Journal of Medicinal Chemistry, 31, p. 1520Anderson, Halat, (1979) J. Med. Chem., 22, p. 977Anderson, McPherson, (1982) J. Med. Chem., 25, p. 84Zalkow, Glinski, Gelbaum, Fleischmann, McGrowan, Gordon, (1985) J. Med. Chem., 28, p. 687Anderson, Corey, (1977) J. Med. Chem., 20, p. 1691Anderson, Halat, Rick, (1980) J. Med. Chem., 23, p. 87Lalezari, Schwartz, (1988) J. Med. Chem., 31, p. 1427Pearson, Bergmeier, Chytra, The Synthesis of Triazole Analogues of Antitumor Dehydropyrrolizidine Alkaloids (1990) Synthesis, p. 156Jones, Sliskovic, (1983) Advances in Heterocyclic Chemistry, 34, p. 79. , A.R. Katritzky, Academic Press, New York (NY)Seebach, Enders, Rolf, Reimund, Reaktion metallierter Nitrosamine mit Nitrilen Eine neue Methode zur Darstellung von υ-Triazolen (1977) Chemische Berichte, 110, p. 1879Regitz, Schwall, Reaktionen CH-aktiver Verbindungen mit Aziden, XXVI Synthese von α-Diazo-iminen und isomeren 1.2.3-Triazolen sowie deren Umwandlung in α-Diazo-immoniumsalze2 (1969) Justus Liebigs Annalen der Chemie, 728, p. 99Baum, Shork, Davies, Smith, Diazotransfer Reactions withp-Acetamidobenzenesulfonyl Azide (1987) Synthetic Communications, 17 (14), p. 1709Celérier, Deloisy, Lhommet, Maitte, Lactim ether chemistry. Cyclic .beta.-enamino ester synthesis (1979) The Journal of Organic Chemistry, 44, p. 3089Chen, Mariano, Little, O'Brien, Huesmann, Electron-transfer-initiated photospirocyclization reactions of .beta.-enaminone-derived allyliminium salts (1984) The Journal of Organic Chemistry, 49 (2), p. 220Coretts, Hindmarsh, Mah, Preparation and properties of 5-nitro-, 7-nitro-, and 5,7-dinitrooxindole (1970) Canadian Journal of Chemistry, 48, p. 3747