90
3 The Reactivity of Nitrile Imines
81. Morrocchi S, Ricca A, Zanarotti A (1970) New features of the reaction between nitrilimines
and arylacetylenes. Tetrahedron Lett 11:3215–3218
82. Huisgen R, Sauer J, Seidel M (1961) Ringöffnungen der Azole, VI. Die Thermolyse 2.5disubstituierter Tetrazole zu Nitriliminen. Chem Ber 94:2503–2509
83. Shou W-G, Yang Y-Y, Wang Y-G (2005) Parallel synthesis of strongly fluorescent Tetraaryl4,5-dihydro-1,2,4-triazoles via 1,3-Dipolar cycloaddition on soluble polymer support.
Synthesis (Stuttg) 2005:3535–3540
84. Sasaki T, Eguchi S, Toi N (1979) Synthesis of adamantane derivatives. 47. Photochemical
synthesis of 4-Azahomoadamant-4-enes and further studies on their reactivity in some
cycloadditions. J Org Chem 44:3711–3715
85. Stájer G, Bernáth G, Szabó AE, Sohár P, Argay G, Kálmán A (1987) Nitrilimine and nitrile
oxide cycloaddition cis-condensed 1,3-dihydrooxazines. Tetrahedron 43:5461–5466
86. Kennewell PD, Miller DJ, Scrowston RM, Westwood R (1994) Reactions of nitrile oxides
and nitrile imines with derivatives of 4,5-dihydrooxazole and 4,5-dihydrothiazole and with
related compounds. J Chem Soc Perkin Trans 1:3563
87. Aversa MC, Ferlazzo A, Giannetto P, Kohnke FH (1986) A convenient synthesis of novel
[1,2,4]Triazolo[4,3-a][1,5]benzodiazepine Derivatives. Synthesis (Stuttg) 230–231
88. Elwan NM, Abdelhadi HA, Abdallah TA, Hassaneen HM (1996) Synthesis of
[1,2,4]Triazolo[3,4-a]isoquinolines and Pyrrolo[2,1-a]isoquinolines using α-Keto
Hydrazonoyl Halides. Tetrahedron 52:3451–3456
89. Donoghue J, Lader M (2010) Usage of benzodiazepines: a review. Int J Psychiatry Clin Pract
14:78–87
90. Molteni G, Broggini G, Pilati T (2002) Diastereoselective Nitrilimine cycloaddition to the
C=N bond of Enantiopure 1,4-Benzodiazepinones. Tetrahedron Asymmetry 13:2491–2495
91. Molteni G, Ponti A (2004) Stereoselective nitrilimine cycloadditions to the CN bond of
enantiopure N-(1-Phenylethyl)-1-arylmethanimines. Tetrahedron Asymmetry 15:3711–3714
92. Yen W-P, Kung F-C, Wong FF (2016) 1,3-dipolar cycloaddition of carbodiimides and
nitrilimines: synthesis and mechanistic study of 5-Amino-1,2,4-triazoles. Eur J Org Chem
2016:2328–2335
93. Tseng W-C, Wang L-Y, Wu T-S, Wong FF (2011) ‘One-Flask’ synthesis to 3,5Disubstituted 1,2,4-Triazoles from aldehydes with hydrazonoyl hydrochlorides via 1,3Dipolar cycloaddition. Tetrahedron 67:5339–5345
94. Huisgen R, Grashey R, Aufderhaar E, Kunz R (1965) 1.3-dipolare cycloadditionen, XIII.
Additionen der Nitrilimine an Oxime, Azine und andere CN-Doppelbindungen. Chem Ber
98:642–649
95. Ferwanah A-RS, Awadallah AM (2005) Reaction of nitrilimines and nitrile oxides with
hydrazines, hydrazones and oximes. Molecules 10:492–507
96. Huisgen R, Grashley R, Knupfer H, Kunz R, Seidel M (1964) 1.3-Dipolare Cycloadditionen,
VI. Anlagerung der Nitrilimine an Azomethine und Isocyanate. Chem Ber 97:1085–1095
97. Liu B, Li X-F, Liu H-C, Yu X-Y (2013) Unexpected nitrilimine cycloaddition of Thiazolo[3,2a]pyrimidine derivatives. Tetrahedron Lett 54:6952–6954
98. Huisgen R, Grashey R, Seidel M, Wallbillich G, Knupfer H, Schmidt R (1962) 1.3-dipolare
Additionen, II. synthase von 1.2.4-Triazolen aus Nitriliminen und Nitrilen. Justus Liebigs
Ann Chem 653:105–113
99. Stille JK, Gotter LD (1968) Polymers from 1,3-dipole addition reactions: a bisnitrilimine
dipole from a bistetrazole precursor. J Polym Sci Part B Polym Lett 6:11–14
100. Stille JK, Harris FW (1968) Polymers from 1,3-dipole addition reactions: the nitrilimine
dipole from acid hydrazide chlorides. J Polym Sci Part A-1 Polym Chem 6:2317–2330
101. Neidlein R, Sui Z (1991) The 1,3-dipolar cycloadditions of nitrile oxides and nitrile imines
to alkyl dicyanoacetates. Helv Chim Acta 74:501–507
102. Garanti L, Scandroglio A, Zecchi G (1976) Synthesis of fused ring 1,2,4-triazoles by
intramolecular cycloaddition of nitrile imines to the nitrile function. J Heterocycl Chem
13:1339–1341
3 The Reactivity of Nitrile Imines
81. Morrocchi S, Ricca A, Zanarotti A (1970) New features of the reaction between nitrilimines
and arylacetylenes. Tetrahedron Lett 11:3215–3218
82. Huisgen R, Sauer J, Seidel M (1961) Ringöffnungen der Azole, VI. Die Thermolyse 2.5disubstituierter Tetrazole zu Nitriliminen. Chem Ber 94:2503–2509
83. Shou W-G, Yang Y-Y, Wang Y-G (2005) Parallel synthesis of strongly fluorescent Tetraaryl4,5-dihydro-1,2,4-triazoles via 1,3-Dipolar cycloaddition on soluble polymer support.
Synthesis (Stuttg) 2005:3535–3540
84. Sasaki T, Eguchi S, Toi N (1979) Synthesis of adamantane derivatives. 47. Photochemical
synthesis of 4-Azahomoadamant-4-enes and further studies on their reactivity in some
cycloadditions. J Org Chem 44:3711–3715
85. Stájer G, Bernáth G, Szabó AE, Sohár P, Argay G, Kálmán A (1987) Nitrilimine and nitrile
oxide cycloaddition cis-condensed 1,3-dihydrooxazines. Tetrahedron 43:5461–5466
86. Kennewell PD, Miller DJ, Scrowston RM, Westwood R (1994) Reactions of nitrile oxides
and nitrile imines with derivatives of 4,5-dihydrooxazole and 4,5-dihydrothiazole and with
related compounds. J Chem Soc Perkin Trans 1:3563
87. Aversa MC, Ferlazzo A, Giannetto P, Kohnke FH (1986) A convenient synthesis of novel
[1,2,4]Triazolo[4,3-a][1,5]benzodiazepine Derivatives. Synthesis (Stuttg) 230–231
88. Elwan NM, Abdelhadi HA, Abdallah TA, Hassaneen HM (1996) Synthesis of
[1,2,4]Triazolo[3,4-a]isoquinolines and Pyrrolo[2,1-a]isoquinolines using α-Keto
Hydrazonoyl Halides. Tetrahedron 52:3451–3456
89. Donoghue J, Lader M (2010) Usage of benzodiazepines: a review. Int J Psychiatry Clin Pract
14:78–87
90. Molteni G, Broggini G, Pilati T (2002) Diastereoselective Nitrilimine cycloaddition to the
C=N bond of Enantiopure 1,4-Benzodiazepinones. Tetrahedron Asymmetry 13:2491–2495
91. Molteni G, Ponti A (2004) Stereoselective nitrilimine cycloadditions to the CN bond of
enantiopure N-(1-Phenylethyl)-1-arylmethanimines. Tetrahedron Asymmetry 15:3711–3714
92. Yen W-P, Kung F-C, Wong FF (2016) 1,3-dipolar cycloaddition of carbodiimides and
nitrilimines: synthesis and mechanistic study of 5-Amino-1,2,4-triazoles. Eur J Org Chem
2016:2328–2335
93. Tseng W-C, Wang L-Y, Wu T-S, Wong FF (2011) ‘One-Flask’ synthesis to 3,5Disubstituted 1,2,4-Triazoles from aldehydes with hydrazonoyl hydrochlorides via 1,3Dipolar cycloaddition. Tetrahedron 67:5339–5345
94. Huisgen R, Grashey R, Aufderhaar E, Kunz R (1965) 1.3-dipolare cycloadditionen, XIII.
Additionen der Nitrilimine an Oxime, Azine und andere CN-Doppelbindungen. Chem Ber
98:642–649
95. Ferwanah A-RS, Awadallah AM (2005) Reaction of nitrilimines and nitrile oxides with
hydrazines, hydrazones and oximes. Molecules 10:492–507
96. Huisgen R, Grashley R, Knupfer H, Kunz R, Seidel M (1964) 1.3-Dipolare Cycloadditionen,
VI. Anlagerung der Nitrilimine an Azomethine und Isocyanate. Chem Ber 97:1085–1095
97. Liu B, Li X-F, Liu H-C, Yu X-Y (2013) Unexpected nitrilimine cycloaddition of Thiazolo[3,2a]pyrimidine derivatives. Tetrahedron Lett 54:6952–6954
98. Huisgen R, Grashey R, Seidel M, Wallbillich G, Knupfer H, Schmidt R (1962) 1.3-dipolare
Additionen, II. synthase von 1.2.4-Triazolen aus Nitriliminen und Nitrilen. Justus Liebigs
Ann Chem 653:105–113
99. Stille JK, Gotter LD (1968) Polymers from 1,3-dipole addition reactions: a bisnitrilimine
dipole from a bistetrazole precursor. J Polym Sci Part B Polym Lett 6:11–14
100. Stille JK, Harris FW (1968) Polymers from 1,3-dipole addition reactions: the nitrilimine
dipole from acid hydrazide chlorides. J Polym Sci Part A-1 Polym Chem 6:2317–2330
101. Neidlein R, Sui Z (1991) The 1,3-dipolar cycloadditions of nitrile oxides and nitrile imines
to alkyl dicyanoacetates. Helv Chim Acta 74:501–507
102. Garanti L, Scandroglio A, Zecchi G (1976) Synthesis of fused ring 1,2,4-triazoles by
intramolecular cycloaddition of nitrile imines to the nitrile function. J Heterocycl Chem
13:1339–1341