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188. Altu˘ g C, Dürüst Y, Elliott MC, Kariuki BM, Rorstad T, Zaal M (2010) Reaction of heterocyclic
enamines with nitrile oxide and nitrilimine precursors. Org Biomol Chem 8:4978
189. Elwahy AHM, Darweesh AF, Shaaban MR (2012) Microwave-assisted synthesis of
Bis(enaminoketones): versatile precursors for novel bis(pyrazoles) via regioselective 1,3dipolar cycloaddition with nitrileimines. J Heterocycl Chem 49:1120–1125
190. Oh LM (2006) Synthesis of celecoxib via 1,3-dipolar cycloaddition. Tetrahedron Lett
47:7943–7946
191. Pinto DJP, Orwat MJ, Koch S, Rossi KA, Alexander RS, Smallwood A, Wong
PC, Rendina AR, Luettgen JM, Knabb RM, He K, Xin B, Wexler RR, Lam PYS
(2007) Discovery of 1-(4-Methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide (Apixaban, BMS-562247), a highly
potent, selective, efficacious, and orally bioavailable inhibitor of blood coagulation F. J Med
Chem 50:5339–5356
192. Oh LM, Wang H, Shilcrat SC, Herrmann RE, Patience DB, Spoors PG, Sisko J (2007)
Development of a scalable synthesis of GSK183390A, a PPAR α/γ agonist. Org Process
Res Dev 11:1032–1042
193. Donohue AC, Pallich S, McCarthy TD (2001) Cycloaddition of nitrile imines to resin-bound
enamines: a solid phase synthesis of 1,4-diarylpyrazoles. J Chem Soc Perkin Trans 1:2817–
2822
194. Hassaneen HME, Hassaneen HM, Elnagdi MH (2004) Enamines in heterocyclic synthesis:
a route to 4-substituted pyrazoles and condensed pyrazoles. Zeitschrift für Naturforsch B
59:1132–1136
195. Donohue SR, Halldin C, Pike VW (2008) A facile and regioselective synthesis of rimonabant
through an enamine-directed 1,3-dipolar cycloaddition. Tetrahedron Lett 49:2789–2791
196. Utecht G, Fruzi´ nski A, Jasi´ nski M (2018) Polysubstituted 3-Trifluoromethylpyrazoles:
regioselective (3 + 2)-cycloaddition of trifluoroacetonitrile imines with enol ethers and
functional group transformations. Org Biomol Chem 16:1252–1257
197. Curtin DY, Alexandrou NE (1963) Reassignment of structures of the Dihydro-v-tetrazines.
Tetrahedron 19:1697–1703
198. Wintner C (1970) Photocyclization of bisphenylazostilbene: an apparent new source of phenyl
imidogen [phenyl nitrene]. Tetrahedron Lett 11:2275–2276
199. Markgraf JH, Brown SH, Kaplinsky MW, Peterson RG (1964) The thermolysis of 5Aryltetrazoles. J Org Chem 29:2629–2632
200. Huisgen R, Aufderhaar E, Wallbillich G (1965) 1.3-dipolare cycloadditionen, XVI: Zur
Bildung von 1.4-Dihydro-tetrazinen aus nitriliminen; 1.4-Diphenyl-1.4-dihydro-1.2.4.5tetrazin und isomere Verbindungen. Chem Ber 98:1476–1486
201. Stille JK, Harris FW (1966) Polymers from 1,3-dipole addition reactions: the nitrilimine
dipole. J Polym Sci Part B Polym Lett 4:333–336
202. George MV, Angadiyavar CS (1971) Photochemical cycloadditions of 1,3-dipolar systems. I.
Additions of N, C-diphenylsydnone and 2,5-diphenyltetrazole. J Org Chem 36:1589–1594
203. Fraser RR, Gurudata HKE (1969) Photolysis of 2-methyl-5-phenyltetrazole. J Org Chem
34:4118–4120
204. Scheiner P, Dinda JF (1970) Product formation in tetrazole photolysis. Tetrahedron 26:2619–
2629
205. Scheiner P, Litchman WM (1972) Tetrazole photochemistry: the question of ringtransposition. J Chem Soc Chem Commun 781
206. Märky M, Meier H, Wunderli A, Heimgartner H, Schmid H, Hansen H-J (1978) On the
photochemistry of sydnones and 1,3,4-oxadiazolin-2-ones. Helv Chim Acta 61:1477–1510
207. Fischer S, Wentrup C (1980) nitrile imide–imidoylnitrene–carbodiimide rearrangement. J
Chem Soc, Chem Commun 502–503
208. Stewart S, Harris R, Jamieson C (2014) Regiospecific synthesis of N2-Aryl 1,2,3-triazoles
from 2,5-disubstituted tetrazoles via photochemically generated nitrile imine intermediates.
Synlett 25:2480–2484
95
187. Altug C, Dürüst Y, Elliott MC (2009) Reactions of alkylidenepyrrolidines with αchlorooximes and α-chlorohydrazones. Tetrahedron Lett 50:7392–7394
188. Altu˘ g C, Dürüst Y, Elliott MC, Kariuki BM, Rorstad T, Zaal M (2010) Reaction of heterocyclic
enamines with nitrile oxide and nitrilimine precursors. Org Biomol Chem 8:4978
189. Elwahy AHM, Darweesh AF, Shaaban MR (2012) Microwave-assisted synthesis of
Bis(enaminoketones): versatile precursors for novel bis(pyrazoles) via regioselective 1,3dipolar cycloaddition with nitrileimines. J Heterocycl Chem 49:1120–1125
190. Oh LM (2006) Synthesis of celecoxib via 1,3-dipolar cycloaddition. Tetrahedron Lett
47:7943–7946
191. Pinto DJP, Orwat MJ, Koch S, Rossi KA, Alexander RS, Smallwood A, Wong
PC, Rendina AR, Luettgen JM, Knabb RM, He K, Xin B, Wexler RR, Lam PYS
(2007) Discovery of 1-(4-Methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide (Apixaban, BMS-562247), a highly
potent, selective, efficacious, and orally bioavailable inhibitor of blood coagulation F. J Med
Chem 50:5339–5356
192. Oh LM, Wang H, Shilcrat SC, Herrmann RE, Patience DB, Spoors PG, Sisko J (2007)
Development of a scalable synthesis of GSK183390A, a PPAR α/γ agonist. Org Process
Res Dev 11:1032–1042
193. Donohue AC, Pallich S, McCarthy TD (2001) Cycloaddition of nitrile imines to resin-bound
enamines: a solid phase synthesis of 1,4-diarylpyrazoles. J Chem Soc Perkin Trans 1:2817–
2822
194. Hassaneen HME, Hassaneen HM, Elnagdi MH (2004) Enamines in heterocyclic synthesis:
a route to 4-substituted pyrazoles and condensed pyrazoles. Zeitschrift für Naturforsch B
59:1132–1136
195. Donohue SR, Halldin C, Pike VW (2008) A facile and regioselective synthesis of rimonabant
through an enamine-directed 1,3-dipolar cycloaddition. Tetrahedron Lett 49:2789–2791
196. Utecht G, Fruzi´ nski A, Jasi´ nski M (2018) Polysubstituted 3-Trifluoromethylpyrazoles:
regioselective (3 + 2)-cycloaddition of trifluoroacetonitrile imines with enol ethers and
functional group transformations. Org Biomol Chem 16:1252–1257
197. Curtin DY, Alexandrou NE (1963) Reassignment of structures of the Dihydro-v-tetrazines.
Tetrahedron 19:1697–1703
198. Wintner C (1970) Photocyclization of bisphenylazostilbene: an apparent new source of phenyl
imidogen [phenyl nitrene]. Tetrahedron Lett 11:2275–2276
199. Markgraf JH, Brown SH, Kaplinsky MW, Peterson RG (1964) The thermolysis of 5Aryltetrazoles. J Org Chem 29:2629–2632
200. Huisgen R, Aufderhaar E, Wallbillich G (1965) 1.3-dipolare cycloadditionen, XVI: Zur
Bildung von 1.4-Dihydro-tetrazinen aus nitriliminen; 1.4-Diphenyl-1.4-dihydro-1.2.4.5tetrazin und isomere Verbindungen. Chem Ber 98:1476–1486
201. Stille JK, Harris FW (1966) Polymers from 1,3-dipole addition reactions: the nitrilimine
dipole. J Polym Sci Part B Polym Lett 4:333–336
202. George MV, Angadiyavar CS (1971) Photochemical cycloadditions of 1,3-dipolar systems. I.
Additions of N, C-diphenylsydnone and 2,5-diphenyltetrazole. J Org Chem 36:1589–1594
203. Fraser RR, Gurudata HKE (1969) Photolysis of 2-methyl-5-phenyltetrazole. J Org Chem
34:4118–4120
204. Scheiner P, Dinda JF (1970) Product formation in tetrazole photolysis. Tetrahedron 26:2619–
2629
205. Scheiner P, Litchman WM (1972) Tetrazole photochemistry: the question of ringtransposition. J Chem Soc Chem Commun 781
206. Märky M, Meier H, Wunderli A, Heimgartner H, Schmid H, Hansen H-J (1978) On the
photochemistry of sydnones and 1,3,4-oxadiazolin-2-ones. Helv Chim Acta 61:1477–1510
207. Fischer S, Wentrup C (1980) nitrile imide–imidoylnitrene–carbodiimide rearrangement. J
Chem Soc, Chem Commun 502–503
208. Stewart S, Harris R, Jamieson C (2014) Regiospecific synthesis of N2-Aryl 1,2,3-triazoles
from 2,5-disubstituted tetrazoles via photochemically generated nitrile imine intermediates.
Synlett 25:2480–2484