32
2 The Generation of Nitrile Imine Derivatives
References
1. Shawali AS, Mosselhi MAN (2003) Hydrazonoyl halides: useful building blocks for the
synthesis of arylazoheterocycles. J Heterocycl Chem 40:725–746
2. Shawali AS, Elwan NM, Awad AM (1997) Kinetics and mechanism of dehydrochlorination of
N-aryl 2-oxo-2-phenylaminoethanehydrazonoyl chlorides and their mass spectra. J Chem Res
0:268–269
3. Huisgen R, Seidel M, Sauer J, McFarland J, Wallbillich G (1959) Communications: the formation of nitrile imines in the thermal breakdown of 2,5-disubstituted tetrazoles. J Org Chem
24:892–893
4. Clovis JS, Eckell A, Huisgen R, Sustmann R (1967) 1.3-dipolare cycloadditionen, XXV. Der
Nachweis des freien Diphenylnitrilimins als Zwischenstufe bei Cycloadditionen. Chem Ber
100:60–70
5. Hegarty AF, Cashman MP, Scott FL (1971) Mechanism of 1,3-dipolar ion formation. J Chem
Soc D Chem Commun 684
6. Hegarty AF, Cashman MP, Scott FL (1972) The kinetics of nitrilimine formation in basecatalysed hydrolysis of hydrazonyl halides. J Chem Soc Perkin Trans 2:44
7. 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
8. Zecchi G, Garanti L, Molteni G (1995) Silver carbonate promoted reaction of hydrazonyl
chlorides with allylic alcohols. Heterocycles 40:777
9. Molteni G (2007) Silver(I) salts as useful reagents in pyrazole synthesis. ARKIVOC 224–246
10. Anderson K, Butler E, Anderson D, Woolley E (1967) The solubility of silver chloride and the
concentrations of silver-containing species in ethanol-water mixtures. J Phys Chem 71:3566–
3569
11. Molteni G, Orlandi M, Broggini G (2000) Nitrilimine cycloadditions in aqueous media. J Chem
Soc, Perkin Trans 1:3742–3745
12. Ramil CP, Lin Q (2014) Photoclick chemistry: a fluorogenic light-triggered in vivo ligation
reaction. Curr Opin Chem Biol 21:89–95
13. Azizian J, Soozangarzadeh S, Jadidi K (2001) Microwave-induced one-pot synthesis of some
new sprio[3H-Indole-3,5’(4’H)-[1,2,4]-triazoline]-2-ones. Synth Commun 31:1069–1073
14. Atir R, Mallouk S, Bougrin K, Soufiaoui M, Laghzizil A (2006) Porous calcium hydroxyapatite
as an efficient catalyst for synthesis of pyrazolines via 1,3-dipolar cycoloaddition under solventfree microwave irradiation. Synth Commun 36:111–120
15. Tewari RS, Parihar P (1981) Halogenation of substituted hydrazones. A facile route for the
synthesis of some new hydrazidoyl halides. J Chem Eng Data 26:418–420
16. Wolkoff P (1975) A new method of preparing hydrazonyl halides. Can J Chem 53:1333–1335
17. Wamhoff H, Zahran M (1987) Dihalogentriphenylphosphoranes in heterocyclic synthesis; 15.1 a simple one-pot-procedure for the generation of Nitrilimines with the aid of
dihalogentriphenyl-phosphoranes: 1,3-dipolar cycloadditions and 1,5-electrocyclizations. Synthesis (Stuttg) 876–879
18. Rai KML, Hassner A (1989) Chlorahine-T in heterocyclic synthesis;1 a simple procedure
for the generation of Nitrilimines and its application to the synthesis of pyrazolines. Synth
Commun 2799–2807
19. Oviedo JJ, de la Cruz P, Garin J, Orduna J, Langa F (2005) Ruthenocene as a new donor
fragment in [60]fullerene–donor dyads. Tetrahedron Lett 46:4781–4784
20. Bamberger E (1898) Zur Kenntniss der Sogenannten Nitroazoparaffine. Berichte der Dtsch
Chem Gesellschaft 31:2626–2635
21. Bamberger E, Grob J (1901) Ueber die Einwirkung von Natriummethylat auf Phenylnitroformaldehydrazon und die Oxydation des Benzaldehydrazons. Berichte der Dtsch Chem
Gesellschaft 34:523–532
22. Garanti L, Zecchi G (1974) Synthesis of 2-substituted 4H-pyrazoIo[5,1-c][1,4]-benzoxazines
from 1-Nitro- and 1-Phenylsulfonyl-N-[2-(2-propynyloxy)-phenyl]-hydrazones. Synthesis
(Stuttg) 814–815
2 The Generation of Nitrile Imine Derivatives
References
1. Shawali AS, Mosselhi MAN (2003) Hydrazonoyl halides: useful building blocks for the
synthesis of arylazoheterocycles. J Heterocycl Chem 40:725–746
2. Shawali AS, Elwan NM, Awad AM (1997) Kinetics and mechanism of dehydrochlorination of
N-aryl 2-oxo-2-phenylaminoethanehydrazonoyl chlorides and their mass spectra. J Chem Res
0:268–269
3. Huisgen R, Seidel M, Sauer J, McFarland J, Wallbillich G (1959) Communications: the formation of nitrile imines in the thermal breakdown of 2,5-disubstituted tetrazoles. J Org Chem
24:892–893
4. Clovis JS, Eckell A, Huisgen R, Sustmann R (1967) 1.3-dipolare cycloadditionen, XXV. Der
Nachweis des freien Diphenylnitrilimins als Zwischenstufe bei Cycloadditionen. Chem Ber
100:60–70
5. Hegarty AF, Cashman MP, Scott FL (1971) Mechanism of 1,3-dipolar ion formation. J Chem
Soc D Chem Commun 684
6. Hegarty AF, Cashman MP, Scott FL (1972) The kinetics of nitrilimine formation in basecatalysed hydrolysis of hydrazonyl halides. J Chem Soc Perkin Trans 2:44
7. 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
8. Zecchi G, Garanti L, Molteni G (1995) Silver carbonate promoted reaction of hydrazonyl
chlorides with allylic alcohols. Heterocycles 40:777
9. Molteni G (2007) Silver(I) salts as useful reagents in pyrazole synthesis. ARKIVOC 224–246
10. Anderson K, Butler E, Anderson D, Woolley E (1967) The solubility of silver chloride and the
concentrations of silver-containing species in ethanol-water mixtures. J Phys Chem 71:3566–
3569
11. Molteni G, Orlandi M, Broggini G (2000) Nitrilimine cycloadditions in aqueous media. J Chem
Soc, Perkin Trans 1:3742–3745
12. Ramil CP, Lin Q (2014) Photoclick chemistry: a fluorogenic light-triggered in vivo ligation
reaction. Curr Opin Chem Biol 21:89–95
13. Azizian J, Soozangarzadeh S, Jadidi K (2001) Microwave-induced one-pot synthesis of some
new sprio[3H-Indole-3,5’(4’H)-[1,2,4]-triazoline]-2-ones. Synth Commun 31:1069–1073
14. Atir R, Mallouk S, Bougrin K, Soufiaoui M, Laghzizil A (2006) Porous calcium hydroxyapatite
as an efficient catalyst for synthesis of pyrazolines via 1,3-dipolar cycoloaddition under solventfree microwave irradiation. Synth Commun 36:111–120
15. Tewari RS, Parihar P (1981) Halogenation of substituted hydrazones. A facile route for the
synthesis of some new hydrazidoyl halides. J Chem Eng Data 26:418–420
16. Wolkoff P (1975) A new method of preparing hydrazonyl halides. Can J Chem 53:1333–1335
17. Wamhoff H, Zahran M (1987) Dihalogentriphenylphosphoranes in heterocyclic synthesis; 15.1 a simple one-pot-procedure for the generation of Nitrilimines with the aid of
dihalogentriphenyl-phosphoranes: 1,3-dipolar cycloadditions and 1,5-electrocyclizations. Synthesis (Stuttg) 876–879
18. Rai KML, Hassner A (1989) Chlorahine-T in heterocyclic synthesis;1 a simple procedure
for the generation of Nitrilimines and its application to the synthesis of pyrazolines. Synth
Commun 2799–2807
19. Oviedo JJ, de la Cruz P, Garin J, Orduna J, Langa F (2005) Ruthenocene as a new donor
fragment in [60]fullerene–donor dyads. Tetrahedron Lett 46:4781–4784
20. Bamberger E (1898) Zur Kenntniss der Sogenannten Nitroazoparaffine. Berichte der Dtsch
Chem Gesellschaft 31:2626–2635
21. Bamberger E, Grob J (1901) Ueber die Einwirkung von Natriummethylat auf Phenylnitroformaldehydrazon und die Oxydation des Benzaldehydrazons. Berichte der Dtsch Chem
Gesellschaft 34:523–532
22. Garanti L, Zecchi G (1974) Synthesis of 2-substituted 4H-pyrazoIo[5,1-c][1,4]-benzoxazines
from 1-Nitro- and 1-Phenylsulfonyl-N-[2-(2-propynyloxy)-phenyl]-hydrazones. Synthesis
(Stuttg) 814–815