92
3 The Reactivity of Nitrile Imines
123. Matsubara Y, Adachi K, Tada H, Kitano K (1996) Synthesis of 1, 3, 4-oxadiazolin-2-ones by
1,3-dipolar addition of carbon dioxide with nitrile imine. Yakugaku Zasshi 116:255–258
124. Guo C-X, Zhang W-Z, Zhang N, Lu X-B (2017) 1,3-dipolar cycloaddition of nitrile imine
with carbon dioxide: access to 1,3,4-oxadiazole-2(3H)-ones. J Org Chem 82:7637–7642
125. Murillo F, Barroso J, de los Santos MG, Ávila G, Pan S, Fernández-Herrera MA, Merino G
(2018) Revisiting the formation mechanism of 1,3,4-oxadiazole-2(3H)-ones from hydrazonyl
chloride and carbon dioxide. J Org Chem 83:13045–13050
126. Caramella P (1968) cycloaddition of furan with nitrilimines. Tetrahedron Lett 9:743–744
127. Fišera ˇ
L, Kovᡠc J, Leško J, Šmahovský V (1981) 1,3-dipolar cycloadditions of heterocycles.
V. Reaction of C-acetyl-N-phenylnitrilimine with furan derivatives. Chem Pap 35:93–104
128. Broggini G, Garanti L, Molteni G, Zecchi G (1998) Dipolarophilic behaviour of the thiophene
ring in intramolecular nitrile imine cycloadditions. J Chem Soc Perkin Trans 1:4103–4106
129. Ruccia M, Vivona N, Cusmano G (1972) cycloadditions in the pyrrole series. Tetrahedron
Lett 13:4703–4706
130. Ruccia M, Vivona N, Cusmano G (1978) Addition reactions of heterocycles. VI. Reactions
of 1,2-dimethylpyrrole and 1-methyl-2-Carbomethoxypyrrole with nitrilimines. J Heterocycl
Chem 15:293–296
131. Moura NMM, Giuntini F, Faustino MAF, Neves MGPMS, Tome AC, Silva AMS, Rakib EM,
Hannioui A, Abouricha S, Roder B, Cavaleiro JAS (2010) 1,3-dipolar cycloaddition of nitrile
imines to meso-tetraarylporphyrins. ARKIVOC 24–33
132. Fu X, Meng Y, Li X, St˛ epie´ n M, Chmielewski PJ (2018) Extension of antiaromatic norcorrole
by cycloaddition. Chem Commun 54:2510–2513
133. Ruccia M, Vivona N, Cusmano G, Marino ML, Piozzi F (1973) Addition reactions of
heterocycles—IV: indoles and nitrilimines. Tetrahedron 29:3159–3164
134. El Azzaoui B, Rachid B, Doumbia ML, Essassi EM, Gornitzka H, Bellan J (2006) Unexpected
opening of benzimidazole derivatives during 1,3-dipolar cycloaddition. Tetrahedron Lett
47:8807–8810
135. Lauria A, Guarcello A, Dattolo G, Almerico AM (2008) Bis-1,2,4-triazolo[4,3-a:3 ,4 -
c]quinoxalines of pharmaceutical interest from 1,3-dipolar cycloaddition. Tetrahedron Lett
49:1847–1850
136. Lauria A, Guarcello A, Macaluso G, Dattolo G, Almerico AM (2009) Reactivity of asymmetric
benzo-condensed diazines with nitrilimine dipoles in the 1,3-dipolar cycloaddition reactions.
Tetrahedron Lett 50:7333–7336
137. Lauria A, Guarcello A, Dattolo G, Almerico A (2010) Study of reactivity in the 1,3dipolar cycloaddition reactions leading to new triazolopyrrolopyrazine ring systems. Synlett
2010:2067–2070
138. Reimlinger H, Vandewalle JJM, King GSD, Lingier WRF, Merényi R (1970) 1.5-Dipolare
Cyclisierungen, III. Kondensierte Triazole aus konjugierten Nitriliminen. Struktur und
Stabilität der Produkte aus N-acylierten cyclischen Amidrazonen und Thionylchlorid. Chem
Ber 103:1918–1933
139. Dubau-Assibat N, Baceiredo A, Bertrand G (1995) Lawesson’s reagent: an efficient 1,3-dipole
trapping agent. J Org Chem 60:3904–3906
140. Zhao H-W, Zhao Y-D, Liu Y-Y, Zhao L-J, Song X-Q, Chen X-Q, Pang H-L, Du J, Feng N-N
(2017) 1,3-dipolar [3 + 3] cycloaddition of α-halohydroxamate-based azaoxyallyl cations
with hydrazonoyl chloride-derived nitrile imines. RSC Adv 7:55106–55109
141. Zhang Y, Liu W, Zhao Z (2013) Nucleophilic trapping nitrilimine generated by photolysis of
diaryltetrazole in aqueous phase. Molecules 19:306–315
142. Li Z, Qian L, Li L, Bernhammer JC, Huynh HV, Lee J-S, Yao SQ (2015) Tetrazole photoclick
chemistry: reinvestigating its suitability as a bioorthogonal reaction and potential applications.
Angew Chem Int Ed Engl 55:2002–2006
143. Csongár C, Grubert L, Tomaschewski G (1988) Photochemistry of Aryl-Substituted Sydnone
IV. and 2H-Tetrazole VIII. Reaction of nitrilimines with phenols. Zeitschrift für Chemie
28:24–25
3 The Reactivity of Nitrile Imines
123. Matsubara Y, Adachi K, Tada H, Kitano K (1996) Synthesis of 1, 3, 4-oxadiazolin-2-ones by
1,3-dipolar addition of carbon dioxide with nitrile imine. Yakugaku Zasshi 116:255–258
124. Guo C-X, Zhang W-Z, Zhang N, Lu X-B (2017) 1,3-dipolar cycloaddition of nitrile imine
with carbon dioxide: access to 1,3,4-oxadiazole-2(3H)-ones. J Org Chem 82:7637–7642
125. Murillo F, Barroso J, de los Santos MG, Ávila G, Pan S, Fernández-Herrera MA, Merino G
(2018) Revisiting the formation mechanism of 1,3,4-oxadiazole-2(3H)-ones from hydrazonyl
chloride and carbon dioxide. J Org Chem 83:13045–13050
126. Caramella P (1968) cycloaddition of furan with nitrilimines. Tetrahedron Lett 9:743–744
127. Fišera ˇ
L, Kovᡠc J, Leško J, Šmahovský V (1981) 1,3-dipolar cycloadditions of heterocycles.
V. Reaction of C-acetyl-N-phenylnitrilimine with furan derivatives. Chem Pap 35:93–104
128. Broggini G, Garanti L, Molteni G, Zecchi G (1998) Dipolarophilic behaviour of the thiophene
ring in intramolecular nitrile imine cycloadditions. J Chem Soc Perkin Trans 1:4103–4106
129. Ruccia M, Vivona N, Cusmano G (1972) cycloadditions in the pyrrole series. Tetrahedron
Lett 13:4703–4706
130. Ruccia M, Vivona N, Cusmano G (1978) Addition reactions of heterocycles. VI. Reactions
of 1,2-dimethylpyrrole and 1-methyl-2-Carbomethoxypyrrole with nitrilimines. J Heterocycl
Chem 15:293–296
131. Moura NMM, Giuntini F, Faustino MAF, Neves MGPMS, Tome AC, Silva AMS, Rakib EM,
Hannioui A, Abouricha S, Roder B, Cavaleiro JAS (2010) 1,3-dipolar cycloaddition of nitrile
imines to meso-tetraarylporphyrins. ARKIVOC 24–33
132. Fu X, Meng Y, Li X, St˛ epie´ n M, Chmielewski PJ (2018) Extension of antiaromatic norcorrole
by cycloaddition. Chem Commun 54:2510–2513
133. Ruccia M, Vivona N, Cusmano G, Marino ML, Piozzi F (1973) Addition reactions of
heterocycles—IV: indoles and nitrilimines. Tetrahedron 29:3159–3164
134. El Azzaoui B, Rachid B, Doumbia ML, Essassi EM, Gornitzka H, Bellan J (2006) Unexpected
opening of benzimidazole derivatives during 1,3-dipolar cycloaddition. Tetrahedron Lett
47:8807–8810
135. Lauria A, Guarcello A, Dattolo G, Almerico AM (2008) Bis-1,2,4-triazolo[4,3-a:3 ,4 -
c]quinoxalines of pharmaceutical interest from 1,3-dipolar cycloaddition. Tetrahedron Lett
49:1847–1850
136. Lauria A, Guarcello A, Macaluso G, Dattolo G, Almerico AM (2009) Reactivity of asymmetric
benzo-condensed diazines with nitrilimine dipoles in the 1,3-dipolar cycloaddition reactions.
Tetrahedron Lett 50:7333–7336
137. Lauria A, Guarcello A, Dattolo G, Almerico A (2010) Study of reactivity in the 1,3dipolar cycloaddition reactions leading to new triazolopyrrolopyrazine ring systems. Synlett
2010:2067–2070
138. Reimlinger H, Vandewalle JJM, King GSD, Lingier WRF, Merényi R (1970) 1.5-Dipolare
Cyclisierungen, III. Kondensierte Triazole aus konjugierten Nitriliminen. Struktur und
Stabilität der Produkte aus N-acylierten cyclischen Amidrazonen und Thionylchlorid. Chem
Ber 103:1918–1933
139. Dubau-Assibat N, Baceiredo A, Bertrand G (1995) Lawesson’s reagent: an efficient 1,3-dipole
trapping agent. J Org Chem 60:3904–3906
140. Zhao H-W, Zhao Y-D, Liu Y-Y, Zhao L-J, Song X-Q, Chen X-Q, Pang H-L, Du J, Feng N-N
(2017) 1,3-dipolar [3 + 3] cycloaddition of α-halohydroxamate-based azaoxyallyl cations
with hydrazonoyl chloride-derived nitrile imines. RSC Adv 7:55106–55109
141. Zhang Y, Liu W, Zhao Z (2013) Nucleophilic trapping nitrilimine generated by photolysis of
diaryltetrazole in aqueous phase. Molecules 19:306–315
142. Li Z, Qian L, Li L, Bernhammer JC, Huynh HV, Lee J-S, Yao SQ (2015) Tetrazole photoclick
chemistry: reinvestigating its suitability as a bioorthogonal reaction and potential applications.
Angew Chem Int Ed Engl 55:2002–2006
143. Csongár C, Grubert L, Tomaschewski G (1988) Photochemistry of Aryl-Substituted Sydnone
IV. and 2H-Tetrazole VIII. Reaction of nitrilimines with phenols. Zeitschrift für Chemie
28:24–25