88
3 The Reactivity of Nitrile Imines
42. Winters MP, Teleha CA, Sui Z (2014) Synthesis of substituted 2,4,5,6Tetrahydrocyclopenta[c]pyrazoles and 2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles by
intramolecular nitrilimine cycloaddition. Tetrahedron Lett 55:2150–2153
43. L’abbé G, Emmers S, Dehaen W, Dyall LK (1994) 5-Chloropyrazole-4-carbaldehydes as
synthons for intramolecular 1,3-dipolar cycloadditions. J Chem Soc Perkin Trans 1:2553–
2558
44. Bruché L, Zecchi G (1989) The intramolecular nitrile imine cycloaddition route to
Pyrazolo[1,5-a][1,4]benzodiazepines. Tetrahedron 45:7427–7432
45. Broggini G, Bruché L, Garanti L, Zecchi G (1994) Medium- and large-ring heterocyclic
systems by intramolecular nitrile imine cycloadditions. J Chem Soc, Perkin Trans 1:433–438
46. Tsuge O, Ueno K, Kanemasa S (1984) Intramolecular 1,3-dipolar cycloadditions to a furan
ring. Chem Lett 13:285–288
47. Sasaki T, Kanematsu K (1971) The chemistry of cyanoacetylenes. Part IX. Preparation
of pyrazole derivatives via 1,3-dipolar cycloaddition reactions of cyanoacetylenes with
diazomethane, N-phenylsydnone, and diphenylnitrilimine. J Chem Soc C Org 2147
48. Meier H, Heimgartner H, Schmid H (1977) Thermische und photochemisch induzierte
intramolekulare, 1,3-dipolare Cycloadditionen von 4-Phenyl-3-(2-allylphenyl)-sydnon.
Vorläufige Mitteilung. 53. Mitteilung über Photoreaktionen. Helv Chim Acta 60:1087–1090
49. Pfoertner K-H, Foricher J (1980) Photoreaktionen des 3-Methyl-4-phenylsydnons. Helv Chim
Acta 63:653–657
50. Jedlovská E, Fišera L, Lévai A, Tóth G, Balázs B (1999) Synthesis of spiropyrazolines via
1,3-dipolar cycloaddition of nitrilimines. J Heterocycl Chem 36:1087–1090
51. Singh A, Loomer AL, Roth GP (2012) Synthesis of oxindolyl pyrazolines and 3-amino
oxindole building blocks via a nitrile imine [3 + 2] cycloaddition strategy. Org Lett
14:5266–5269
52. Rouatbi F, Mhiri C, Askri M, Knorr M, Rousselin Y, Kubicki MM (2017) Regioselective
synthesis of mono- and dispiropyrazoline derivatives via 1,3-dipolar cycloaddition with
nitrilimines. J Heterocycl Chem 54:1152–1160
53. Herrera R, Nagarajan A, Morales MA, Méndez F, Jiménez-Vázquez HA, Zepeda LG, Tamariz
J (2001) Regio- and stereoselectivity of captodative olefins in 1,3-dipolar cycloadditions.
A DFT/HSAB theory rationale for the observed regiochemistry of nitrones. J Org Chem
66:1252–1263
54. Nagarajan A, Zepeda G, Tamariz J (1996) Highly selective 1,3-dipolar cycloadditions of
captodative olefins 1-acetylvinyl carboxylates to diverse dipoles. Tetrahedron Lett 37:6835–
6838
55. Barluenga J, Fernández-Marí F, González R, Aguilar E, Revelli GA, Viado AL, Fañanás FJ,
Olano B (2000) α, β-unsaturated fischer carbene complexes vs. 1,3-dipoles: reactions with
nitrones and nitrilimines. Eur J Org Chem 2000:1773–1783
56. Barluenga J, Fernández-Marí F, Aguilar E, Viado AL, Olano B (1998) First highly regio- and
diastereoselective synthesis of 2-pyrazolines by [3 + 2] cycloaddition of chiral non-racemic
fischer carbene complexes with nitrilimines. Tetrahedron Lett 39:4887–4890
57. Espildora E, Delgado JL, de la Cruz P, de la Hoz A, Lopez-Arza V, Langa F (2002) Synthesis
and properties of Pyrazolino[60]fullerene-donor systems. Tetrahedron 58:5821–5826
58. Padwa A, Craig SP, Chiacchio U, Kline DN (1988) Site selectivity in the reactions of various
1,3-dipoles with (Phenylsulfonyl)-1,2-propadiene. J Org Chem 53:2232–2238
59. Bruché L, Zecchi G (1987) Base-promoted cyclisation of hydrazonoyl chlorides bearing an
alkynylsulphonyl group. J Chem Soc, Perkin Trans 1:399–400
60. Broggini G, Molteni G (2000) Dipolarophilic behaviour of (Arylsulfonyl)allenes towards
nitrilimines. J Chem Soc Perkin Trans 1:1685–1689
61. Liu H, Jia H, Wang B, Xiao Y, Guo H (2017) Synthesis of spirobidihydropyrazole through
double 1,3-dipolar cycloaddition of nitrilimines with allenoates. Org Lett 19:4714–4717
62. Utecht G, Mlosto´ n G, Jasi´ nski M (2018) A Straightforward access to trifluoromethylated
spirobipyrazolines through a double (3 + 2)-cycloaddition of fluorinated nitrile imines with
alkoxyallenes. Synlett 29:1753–1758
3 The Reactivity of Nitrile Imines
42. Winters MP, Teleha CA, Sui Z (2014) Synthesis of substituted 2,4,5,6Tetrahydrocyclopenta[c]pyrazoles and 2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles by
intramolecular nitrilimine cycloaddition. Tetrahedron Lett 55:2150–2153
43. L’abbé G, Emmers S, Dehaen W, Dyall LK (1994) 5-Chloropyrazole-4-carbaldehydes as
synthons for intramolecular 1,3-dipolar cycloadditions. J Chem Soc Perkin Trans 1:2553–
2558
44. Bruché L, Zecchi G (1989) The intramolecular nitrile imine cycloaddition route to
Pyrazolo[1,5-a][1,4]benzodiazepines. Tetrahedron 45:7427–7432
45. Broggini G, Bruché L, Garanti L, Zecchi G (1994) Medium- and large-ring heterocyclic
systems by intramolecular nitrile imine cycloadditions. J Chem Soc, Perkin Trans 1:433–438
46. Tsuge O, Ueno K, Kanemasa S (1984) Intramolecular 1,3-dipolar cycloadditions to a furan
ring. Chem Lett 13:285–288
47. Sasaki T, Kanematsu K (1971) The chemistry of cyanoacetylenes. Part IX. Preparation
of pyrazole derivatives via 1,3-dipolar cycloaddition reactions of cyanoacetylenes with
diazomethane, N-phenylsydnone, and diphenylnitrilimine. J Chem Soc C Org 2147
48. Meier H, Heimgartner H, Schmid H (1977) Thermische und photochemisch induzierte
intramolekulare, 1,3-dipolare Cycloadditionen von 4-Phenyl-3-(2-allylphenyl)-sydnon.
Vorläufige Mitteilung. 53. Mitteilung über Photoreaktionen. Helv Chim Acta 60:1087–1090
49. Pfoertner K-H, Foricher J (1980) Photoreaktionen des 3-Methyl-4-phenylsydnons. Helv Chim
Acta 63:653–657
50. Jedlovská E, Fišera L, Lévai A, Tóth G, Balázs B (1999) Synthesis of spiropyrazolines via
1,3-dipolar cycloaddition of nitrilimines. J Heterocycl Chem 36:1087–1090
51. Singh A, Loomer AL, Roth GP (2012) Synthesis of oxindolyl pyrazolines and 3-amino
oxindole building blocks via a nitrile imine [3 + 2] cycloaddition strategy. Org Lett
14:5266–5269
52. Rouatbi F, Mhiri C, Askri M, Knorr M, Rousselin Y, Kubicki MM (2017) Regioselective
synthesis of mono- and dispiropyrazoline derivatives via 1,3-dipolar cycloaddition with
nitrilimines. J Heterocycl Chem 54:1152–1160
53. Herrera R, Nagarajan A, Morales MA, Méndez F, Jiménez-Vázquez HA, Zepeda LG, Tamariz
J (2001) Regio- and stereoselectivity of captodative olefins in 1,3-dipolar cycloadditions.
A DFT/HSAB theory rationale for the observed regiochemistry of nitrones. J Org Chem
66:1252–1263
54. Nagarajan A, Zepeda G, Tamariz J (1996) Highly selective 1,3-dipolar cycloadditions of
captodative olefins 1-acetylvinyl carboxylates to diverse dipoles. Tetrahedron Lett 37:6835–
6838
55. Barluenga J, Fernández-Marí F, González R, Aguilar E, Revelli GA, Viado AL, Fañanás FJ,
Olano B (2000) α, β-unsaturated fischer carbene complexes vs. 1,3-dipoles: reactions with
nitrones and nitrilimines. Eur J Org Chem 2000:1773–1783
56. Barluenga J, Fernández-Marí F, Aguilar E, Viado AL, Olano B (1998) First highly regio- and
diastereoselective synthesis of 2-pyrazolines by [3 + 2] cycloaddition of chiral non-racemic
fischer carbene complexes with nitrilimines. Tetrahedron Lett 39:4887–4890
57. Espildora E, Delgado JL, de la Cruz P, de la Hoz A, Lopez-Arza V, Langa F (2002) Synthesis
and properties of Pyrazolino[60]fullerene-donor systems. Tetrahedron 58:5821–5826
58. Padwa A, Craig SP, Chiacchio U, Kline DN (1988) Site selectivity in the reactions of various
1,3-dipoles with (Phenylsulfonyl)-1,2-propadiene. J Org Chem 53:2232–2238
59. Bruché L, Zecchi G (1987) Base-promoted cyclisation of hydrazonoyl chlorides bearing an
alkynylsulphonyl group. J Chem Soc, Perkin Trans 1:399–400
60. Broggini G, Molteni G (2000) Dipolarophilic behaviour of (Arylsulfonyl)allenes towards
nitrilimines. J Chem Soc Perkin Trans 1:1685–1689
61. Liu H, Jia H, Wang B, Xiao Y, Guo H (2017) Synthesis of spirobidihydropyrazole through
double 1,3-dipolar cycloaddition of nitrilimines with allenoates. Org Lett 19:4714–4717
62. Utecht G, Mlosto´ n G, Jasi´ nski M (2018) A Straightforward access to trifluoromethylated
spirobipyrazolines through a double (3 + 2)-cycloaddition of fluorinated nitrile imines with
alkoxyallenes. Synlett 29:1753–1758