How to cite this paper
Roohi, L., Afghan, A & Baradarani, M. (2013). Vilsmeier-Haack reagent: A facile synthesis of 2-(4-chloro-3,3-dimethyl-7-phenoxyindolin-2-ylidene)malonaldehyde and transformation into different heterocyclic compounds.Current Chemistry Letters, 2(4), 187-196.
Refrences
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2. Jones, G.; Stanford, S. P. (2000). The Vilsmeier reaction of non-aromatic compounds. Org. React., 56, 355-659.
3. Jones, G.; Stanford, S. P. (1997). The Vilsmeier Reaction of Fully Conjugated Carbocycles and Heterocycles. Org. React., 49, 1.
4. Newman, M. S.; Sujeeth, P. K. (1978). Conversion of aromatic and .alpha.,.beta.-unsaturated aldehydes to dichlorides by thionyl chloride and dimethylformamide. J. Org. Chem., 43, 4367–4369.
5. Amaresh. A. A.; Perumal P. P. (1998). A novel one-pot synthesis of 2-aminoquinolines from arylazidoketones by cyclization under Vilsmeier conditions. Tetrahedron, 54, 14327–14340.
6. Zhao, L.; Liang, F.; Bie, X.;Sun, S. and Liu, Q. (2006). Efficient Synthesis of Highly Functionalized Dihydropyrido[2,3-d]pyrimidines by a Double Annulation Strategy from ?-Alkenoyl-?-carbamoyl Ketene-(S,S)-acetals. J. Org. Chem., 71, 1094–1098.
7. Reddy, M. P.; Rao, G. S. K. (1981). Applications of the Vilsmeier reaction. 13. Vilsmeier approach to polycyclic aromatic hydrocarbons. J. Org. Chem., 46, 5371-5373.
8. Church, R.; Trust, R.; Albright, J. D.; Powell, D. W. (1995). New Synthetic Routes to 3-, 5-, and 6-Aryl-2-chloropyridines. J. Org. Chem., 60, 3750-3758.
9. Mittelbach, M.; Junek, H. Syntheses with nitriles. (1982). 3,5-Dicyanopyridine derivatives by vilsmeier formylation of malononitrile and tetracyanopropenides. J. Heterocycl. Chem., 19, 1021-1024.
10. Amaresh, R. R.; Perumal, P. T. (1995). Ring opening of chalcone epoxides with vilsmeier reagent. Tetrahedron Lett., 36, 7287-7288.
11. Anderson, D. J. (1986). A reinvestigation of the Vilsmeier reaction of 3-phenyl-5-isoxazolinone. Isolation of 1,3-oxazin-6-ones. J. Org. Chem., 51, 945-947.
12. Fritz, H. (1959). Uber ?.B-unges?ttigte B-Anilino-carbonyl-Verbindungen als Mode- llsubstanzen für den Chromophor von C-Curarin-III (C-Fluorocurarin) Chem. Ber., 92, 1809-1817.
13. Baradarani, M. M.; Afghan, A.; Zebarjadi F.; Hasanzadeh K. and Joule , J. A. (2006). The synthesis of 3,3-dimethyl-2-(1-aryl-1H-pyrazol-4-yl)-3H-indoles. J. Heterocyclic Chem., 43, 1591-1595.
14. Rashidi A.; Baradarani, M. M. and Joule, J. A. (2011). Synthesis of 2,2?-bis(1-(2-aryl)-1H-pyrazol-4-yl)-3,3,3?,3?-tetramethyl-3H,3?H-5,5?-biindoles and 2,7-bis(1-(3-aryl)-1H-pyrazol-4-yl)-1,1,6,6-tetramethyl-1,6-dihydroindolo[7,6-g]indoles. Arkivoc, (ii), 252-259.
15. Rashidi A.; Afghan, A.; Baradarani M. M.; Joule, J. A. (2009). The Synthesis of 4-(3,3-Dimethyl-3H-pyrrolo[2,3-f]quinolin-2-yl)pyrazoles and 4-(3,3-Dimethyl-3H-pyrrolo[3,2-h] quinolin-2-yl)pyrazoles. J. Heterocyclic Chem., 46, 428-431.
16. Simon, C.; Constantieux, T. and Rodriguez, J. (2004) Utilisation of 1,3-Dicarbonyl Derivatives in Multicomponent Reactions Eur. J. Org. Chem., 4957-4980.
17. Penning, T. D.; Talley, J. J.; Bertenshaw, S. R. et al. (1997). Synthesis and Biological Evaluation of the 1.5 Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors: Identification of 4-[5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazole-1-yl]benzenesulfonamide(SC-58634, Celecoxib). J. Med. Chem. 40 (9): 1347–1365.
18. Helliwell, M.; Baradarani, M. M.; Alyari, M.; Afghan, A. and Joule J. A. (2012). 2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene)-2-cyanoacetamide ActaCrystallo- graphica Section E, E68, o234.
2. Jones, G.; Stanford, S. P. (2000). The Vilsmeier reaction of non-aromatic compounds. Org. React., 56, 355-659.
3. Jones, G.; Stanford, S. P. (1997). The Vilsmeier Reaction of Fully Conjugated Carbocycles and Heterocycles. Org. React., 49, 1.
4. Newman, M. S.; Sujeeth, P. K. (1978). Conversion of aromatic and .alpha.,.beta.-unsaturated aldehydes to dichlorides by thionyl chloride and dimethylformamide. J. Org. Chem., 43, 4367–4369.
5. Amaresh. A. A.; Perumal P. P. (1998). A novel one-pot synthesis of 2-aminoquinolines from arylazidoketones by cyclization under Vilsmeier conditions. Tetrahedron, 54, 14327–14340.
6. Zhao, L.; Liang, F.; Bie, X.;Sun, S. and Liu, Q. (2006). Efficient Synthesis of Highly Functionalized Dihydropyrido[2,3-d]pyrimidines by a Double Annulation Strategy from ?-Alkenoyl-?-carbamoyl Ketene-(S,S)-acetals. J. Org. Chem., 71, 1094–1098.
7. Reddy, M. P.; Rao, G. S. K. (1981). Applications of the Vilsmeier reaction. 13. Vilsmeier approach to polycyclic aromatic hydrocarbons. J. Org. Chem., 46, 5371-5373.
8. Church, R.; Trust, R.; Albright, J. D.; Powell, D. W. (1995). New Synthetic Routes to 3-, 5-, and 6-Aryl-2-chloropyridines. J. Org. Chem., 60, 3750-3758.
9. Mittelbach, M.; Junek, H. Syntheses with nitriles. (1982). 3,5-Dicyanopyridine derivatives by vilsmeier formylation of malononitrile and tetracyanopropenides. J. Heterocycl. Chem., 19, 1021-1024.
10. Amaresh, R. R.; Perumal, P. T. (1995). Ring opening of chalcone epoxides with vilsmeier reagent. Tetrahedron Lett., 36, 7287-7288.
11. Anderson, D. J. (1986). A reinvestigation of the Vilsmeier reaction of 3-phenyl-5-isoxazolinone. Isolation of 1,3-oxazin-6-ones. J. Org. Chem., 51, 945-947.
12. Fritz, H. (1959). Uber ?.B-unges?ttigte B-Anilino-carbonyl-Verbindungen als Mode- llsubstanzen für den Chromophor von C-Curarin-III (C-Fluorocurarin) Chem. Ber., 92, 1809-1817.
13. Baradarani, M. M.; Afghan, A.; Zebarjadi F.; Hasanzadeh K. and Joule , J. A. (2006). The synthesis of 3,3-dimethyl-2-(1-aryl-1H-pyrazol-4-yl)-3H-indoles. J. Heterocyclic Chem., 43, 1591-1595.
14. Rashidi A.; Baradarani, M. M. and Joule, J. A. (2011). Synthesis of 2,2?-bis(1-(2-aryl)-1H-pyrazol-4-yl)-3,3,3?,3?-tetramethyl-3H,3?H-5,5?-biindoles and 2,7-bis(1-(3-aryl)-1H-pyrazol-4-yl)-1,1,6,6-tetramethyl-1,6-dihydroindolo[7,6-g]indoles. Arkivoc, (ii), 252-259.
15. Rashidi A.; Afghan, A.; Baradarani M. M.; Joule, J. A. (2009). The Synthesis of 4-(3,3-Dimethyl-3H-pyrrolo[2,3-f]quinolin-2-yl)pyrazoles and 4-(3,3-Dimethyl-3H-pyrrolo[3,2-h] quinolin-2-yl)pyrazoles. J. Heterocyclic Chem., 46, 428-431.
16. Simon, C.; Constantieux, T. and Rodriguez, J. (2004) Utilisation of 1,3-Dicarbonyl Derivatives in Multicomponent Reactions Eur. J. Org. Chem., 4957-4980.
17. Penning, T. D.; Talley, J. J.; Bertenshaw, S. R. et al. (1997). Synthesis and Biological Evaluation of the 1.5 Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors: Identification of 4-[5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazole-1-yl]benzenesulfonamide(SC-58634, Celecoxib). J. Med. Chem. 40 (9): 1347–1365.
18. Helliwell, M.; Baradarani, M. M.; Alyari, M.; Afghan, A. and Joule J. A. (2012). 2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene)-2-cyanoacetamide ActaCrystallo- graphica Section E, E68, o234.