1-(2,5-Dichlorophenyl)hydrazine was converted via Fischer synthesis with isopropylmethylketone into 4,7-dichloro-2,3,3-trimethyl-3H-indole. Exposure of the indolenine to the vilsmeier reagent produced amino methylene malondialdehyde which reacted with hydrazine, arylhydrazine, urea, cyanoacetamide and thiourea to give pyrazols, pyrimidones and thiopyrimidone, respectively.

Mohammadnejad Aghdam, R., Baradarani, M.M., & Afghan, A. (2013). Synthesis of new heterocyclic compounds using 2-(4,7-dichloro-3,3-dimethyl-.Current Chemistry Letters, 2(1), 13-20.

1. Friedel, M. C. (1894) Nor une nouvelle serie de matieres colorants. Bull. Soc. Chim. Fr., 11, 1027-1038.

2. Fischer, O., Muller, A. and Vilsmeier, A. (1925) Über die Einwirkung von Phosphoroxychlorid auf Methyl- (Äthyl-) acetanilid. Synthesen von γ-Chlorisochinocyaninen. J. Prakt. Chem., 109, 69-87.

3. Vilsmeier, A., Haack, A. (1927) Über die Einwirkung von Halogenphosphor auf Alkyl-formanilide. Eine neue Methode zur Darstellung sekundärer und tertiärer p-Alkylamino-benzaldehyde. Chem. Ber., 60, 119-122.

4. Arnold, Z. and Zemlicka, J. (1959) Synthetische Reaktionen von Dimethylformamid. III. Darstellung von ß-Chlorvinylaldehyden. Collect. Czech. Chem. Comm., 24, 2378-2384.



5. Arnold Z. and Zemlicka, J. (1959) Synthetische Reaktionen von Dimethylformamid. IV. Darstellung von ß-Chlorvinylaldehyden aus Carbonylverbindungen. Collect. Czech. Chem. Comm., 24: 2385-2392.

6. Arnold, Z. and Zemlicka, J. (1960) Synthetische Reaktionen von Dimethylformamid. VII. Darstellung von Triformylmethan. Collect. Czech Chem. Comm., 25, 1318-1323.



7. Cheng, Y., Yang, H. B., Liu, B., Meth-Cohn, O., Watkin, D. and Humphries, S. (2003) A Simple One-Pot Reaction to the Bis-dibenzo[b,f][1,5]diazocines: Useful Precursors­ of Novel Macrocycles. Synthesis, 2839-2843.

8. Chu-Yi ,Y., Taylor, D. L. and Meth-Cohn, O. (1999) Pseudo Vilsmeier reagents a new protocol for regiospecific C-C bond formation in pyridines Tetrahedron Lett., 40, 6661-6664.

9. Cheng, Y., Meth-Cohn, O. and Taylor, D. (1998) Vilsmeier formylation of tert-anilines: dibenzo[, ] [1,5]diazocines and quinazolinium salts via the ‘t-amino effect’. J. Chem. Soc., Perkin Trans. 1, 1257-1262.



10. Amaresh, R. R. and Perumal, P. T. (1999) A new and convenient synthesis of 2-imino-2H-pyrancarboxaldehydes from β-ketoamides using Vilsmeier reagent. Tetrahedron, 55, 8083-8094.

11. Amaresh, R. R. and Perumal, P. T. (1998) A novel one-pot synthesis of 2-aminoquinolines from arylazidoketones by cyclization under Vilsmeier conditions. Tetrahedron, 54, 14327-14340.

12. Majo, V. J. and Perumal, P. T. (1996) One-Pot Synthesis of Heterocyclic β-Chlorovinyl Aldehydes Using Vilsmeier Reagent. J. Org. Chem., 61, 6523-6525.

13. Nagarajan, R. and Perumal, P.T. (2004) A Short Route to Heteroarylcarbazoles: Synthesis of New Pyrazolylcarbazoles and Carbazolylquinolines. Synthesis, 1269-1273.

14. 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.

15. Rashidi, A., Afghan, A., Baradarani, M. M., and 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. Alyari, M., Baradarani, M. M., Afghan, A. and Joule, J. A. (2012) The synthesis of new heterocycles using 2-(4-chloro-1,3-dihydro-3,3,7-trimethyl-2H-indol-2-ylidene)propanedial. J. Heterocyclic Chem., in press.

17. Afghan, A., Roohi, L. , Baradarani, M. M. and Joule, J. A. (2012) Synthesis of New Heterocyclic Compounds Using 2-(3,3-dimethyl-1H-pyrroloisoquinolin-2(3H)-ylidene) malonaldehydes. J. Heterocyclic Chem., in press.