94
3 The Reactivity of Nitrile Imines
166. Moderhack D, Lorke M (1987) 1,2,4-trisubstituted 1,2,3-triazolium salts from nitrilimines
and isocyanides. Heterocycles 26:1751
167. Moderhack D, Lorke M, Ernst L, Schomburg D (1994) Zur Reaktion von Isocyaniden mit
Nitriliminen. Chem Ber 127:1633–1639
168. Moderhack D, Daoud A, Jones PG (2002) The behaviour of nitrilimines towards ethyl
isocyanoacetate. Monatshefte für Chemie/Chem Mon 133:1165–1175
169. Moderhack D, Daoud A (2003) 1,2,3- and 1,2,4-triazolium salts, pyrazoles, and quinoxalines
from diarylnitrilimines and isocyanides: a study of the scope. J Heterocycl Chem 40:625–637
170. Giustiniano M, Novellino E, Tron G (2016) Nitrile N-oxides and nitrile imines as new fuels
for the discovery of novel isocyanide-based multicomponent reactions. Synthesis (Stuttg)
48:2721–2731
171. Wang Z (2010) Passerini Reaction. In: Comprehensive organic name reactions and reagents.
Wiley Inc., Hoboken, NJ, USA
172. Giustiniano M, Meneghetti F, Mercalli V, Varese M, Giustiniano F, Novellino E, Tron GC
(2014) Synthesis of aminocarbonyl N-acylhydrazones by a three-component reaction of
isocyanides, hydrazonoyl chlorides, and carboxylic acids. Org Lett 16:5332–5335
173. Giustiniano M, Mercalli V, Amato J, Novellino E, Tron GC (2015) Exploiting the electrophilic
and nucleophilic dual role of nitrile imines: one-pot, three-component synthesis of Furo[2,3d]pyridazin-4(5H)-ones. Org Lett 17:3964–3967
174. Giustiniano M, Mercalli V, Novellino E, Tron GC (2016) An efficient synthesis of 1arylindazole-3-carboxamides using nitrile imines, isocyanides and 2-hydroxymethylbenzoic
acid, followed by a chemoselective Buchwald-Hartwig intramolecular cyclization. RSC Adv
6:34913–34920
175. Soeta T, Takashita S, Sakata Y, Ukaji Y (2016) Ugi-type multicomponent reaction of nitrile
imines, isocyanides, and isocyanates: effective synthesis of 1,2,4-triazinedione derivatives.
Asian J Org Chem 5:1041–1047
176. Dalla Croce P, Del Buttero P, Licandro E, Maiorana S (1979) Synthesis of
Arylazomethylenetriphenylphosphoranes from Arylhydrazonoyl chlorides (via Nitrilimines
in situ) and Triphenylphosphine. Synthesis (Stuttg) 299–300
177. Trishin YG, Namestnikov VI, Belsky VK (1990) Reaction of 2-(4,5-Dihydrofur-3-yl)1,3-Diphenyl-1,3-Diaza-2-2λ3-phospholidine with C, N-Diphenylnitrilimine with C, NDiphenylnitrilimine. Russ Chem Bull 49:129–131
178. Trishin YG, Namestnikov VI, Gonchar TV (2005) Reactions of 2-(4,5-Dihydro-3-Furyl)-1,3diphenyl-1,3-Diaza-2λ3-phospholidine and 4,5-dihydro-3-furylphosphonous diamides with
nitrile imines. Russ Chem Bull 54:1637–1641
179. Trishin YG, Gozhina OV, Tamm LA, Stash AI, Zavodnik VE, Belskii
VK (2008) Synthesis and molecular structure of [2,3,4,5-tetrafluoro-6-(pmethoxyphenylamino)phenyl]diphenylphosphine. Russ J Gen Chem 78:1172–1176
180. Alemagna A, Garanti L, Licandro E, Zecchi G (1984) Stereochemical aspects
of base-promoted reactions of o-alkenyl substituted arylhydrazonoyl chlorides with
triphenylphosphine. Tetrahedron 40:2165–2170
181. Wulff J, Huisgen R (1969) Reaktionen der Methylenphosphorane mit weiteren 1.3-Dipolen
sowie mit Styroloxid. Chem Ber 102:1841–1847
182. Livingstone K, Bertrand S, Mowat J, Jamieson C (2019) Metal-free C-C bond formation via
coupling of nitrile imines and boronic acids. Chem Sci 10:10412–10416
183. Petasis NA, Akritopoulou I (1993) The boronic acid mannich reaction: a new method for the
synthesis of geometrically pure allylamines. Tetrahedron Lett 34:583–586
184. Wu P, Givskov M, Nielsen TE (2019) Reactivity and synthetic applications of multicomponent
petasis reactions. Chem Rev 119:11245–11290
185. Awad EM, Elwan NM, Hassaneen HM, Linden A, Heimgartner H (2001) Synthesis and
reactivity of 2-(6,7-Diethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile towards Hydrazonoyl
Halides. Helv Chim Acta 84:1172–1180
186. Miao W-S, Xiong F, Wang M-X, Huang Z-T (2000) Nucleophilic Reaction of heterocyclic
enamines with nitrile imine 1,3-Dipoles. Synth Commun 30:3255–3265
3 The Reactivity of Nitrile Imines
166. Moderhack D, Lorke M (1987) 1,2,4-trisubstituted 1,2,3-triazolium salts from nitrilimines
and isocyanides. Heterocycles 26:1751
167. Moderhack D, Lorke M, Ernst L, Schomburg D (1994) Zur Reaktion von Isocyaniden mit
Nitriliminen. Chem Ber 127:1633–1639
168. Moderhack D, Daoud A, Jones PG (2002) The behaviour of nitrilimines towards ethyl
isocyanoacetate. Monatshefte für Chemie/Chem Mon 133:1165–1175
169. Moderhack D, Daoud A (2003) 1,2,3- and 1,2,4-triazolium salts, pyrazoles, and quinoxalines
from diarylnitrilimines and isocyanides: a study of the scope. J Heterocycl Chem 40:625–637
170. Giustiniano M, Novellino E, Tron G (2016) Nitrile N-oxides and nitrile imines as new fuels
for the discovery of novel isocyanide-based multicomponent reactions. Synthesis (Stuttg)
48:2721–2731
171. Wang Z (2010) Passerini Reaction. In: Comprehensive organic name reactions and reagents.
Wiley Inc., Hoboken, NJ, USA
172. Giustiniano M, Meneghetti F, Mercalli V, Varese M, Giustiniano F, Novellino E, Tron GC
(2014) Synthesis of aminocarbonyl N-acylhydrazones by a three-component reaction of
isocyanides, hydrazonoyl chlorides, and carboxylic acids. Org Lett 16:5332–5335
173. Giustiniano M, Mercalli V, Amato J, Novellino E, Tron GC (2015) Exploiting the electrophilic
and nucleophilic dual role of nitrile imines: one-pot, three-component synthesis of Furo[2,3d]pyridazin-4(5H)-ones. Org Lett 17:3964–3967
174. Giustiniano M, Mercalli V, Novellino E, Tron GC (2016) An efficient synthesis of 1arylindazole-3-carboxamides using nitrile imines, isocyanides and 2-hydroxymethylbenzoic
acid, followed by a chemoselective Buchwald-Hartwig intramolecular cyclization. RSC Adv
6:34913–34920
175. Soeta T, Takashita S, Sakata Y, Ukaji Y (2016) Ugi-type multicomponent reaction of nitrile
imines, isocyanides, and isocyanates: effective synthesis of 1,2,4-triazinedione derivatives.
Asian J Org Chem 5:1041–1047
176. Dalla Croce P, Del Buttero P, Licandro E, Maiorana S (1979) Synthesis of
Arylazomethylenetriphenylphosphoranes from Arylhydrazonoyl chlorides (via Nitrilimines
in situ) and Triphenylphosphine. Synthesis (Stuttg) 299–300
177. Trishin YG, Namestnikov VI, Belsky VK (1990) Reaction of 2-(4,5-Dihydrofur-3-yl)1,3-Diphenyl-1,3-Diaza-2-2λ3-phospholidine with C, N-Diphenylnitrilimine with C, NDiphenylnitrilimine. Russ Chem Bull 49:129–131
178. Trishin YG, Namestnikov VI, Gonchar TV (2005) Reactions of 2-(4,5-Dihydro-3-Furyl)-1,3diphenyl-1,3-Diaza-2λ3-phospholidine and 4,5-dihydro-3-furylphosphonous diamides with
nitrile imines. Russ Chem Bull 54:1637–1641
179. Trishin YG, Gozhina OV, Tamm LA, Stash AI, Zavodnik VE, Belskii
VK (2008) Synthesis and molecular structure of [2,3,4,5-tetrafluoro-6-(pmethoxyphenylamino)phenyl]diphenylphosphine. Russ J Gen Chem 78:1172–1176
180. Alemagna A, Garanti L, Licandro E, Zecchi G (1984) Stereochemical aspects
of base-promoted reactions of o-alkenyl substituted arylhydrazonoyl chlorides with
triphenylphosphine. Tetrahedron 40:2165–2170
181. Wulff J, Huisgen R (1969) Reaktionen der Methylenphosphorane mit weiteren 1.3-Dipolen
sowie mit Styroloxid. Chem Ber 102:1841–1847
182. Livingstone K, Bertrand S, Mowat J, Jamieson C (2019) Metal-free C-C bond formation via
coupling of nitrile imines and boronic acids. Chem Sci 10:10412–10416
183. Petasis NA, Akritopoulou I (1993) The boronic acid mannich reaction: a new method for the
synthesis of geometrically pure allylamines. Tetrahedron Lett 34:583–586
184. Wu P, Givskov M, Nielsen TE (2019) Reactivity and synthetic applications of multicomponent
petasis reactions. Chem Rev 119:11245–11290
185. Awad EM, Elwan NM, Hassaneen HM, Linden A, Heimgartner H (2001) Synthesis and
reactivity of 2-(6,7-Diethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile towards Hydrazonoyl
Halides. Helv Chim Acta 84:1172–1180
186. Miao W-S, Xiong F, Wang M-X, Huang Z-T (2000) Nucleophilic Reaction of heterocyclic
enamines with nitrile imine 1,3-Dipoles. Synth Commun 30:3255–3265