Lewis acid catalysed Cyclyzation of Amino alcohol and Cyanoester ; 8-chloroisoindolo[1,2-b]quinazolin-12(10H)-one
SyntheticPage 490
DOI:
10.1039/SP490
Submitted Mar 28, 2011, published Apr 01, 2011
Abir Kumar Pal (
abirchem2@yahoo.com)
A contribution from
Dr. Reddys Laboratory, India
Chemicals Used
2-amino-5-chlorobenzyl alcohol (Alfa-Aesar)
Methyl 2-cyanobenzoate (see Referance)
BF3.Et2O (SRL) (48-50% BF3)
Dichloromethane
Procedure
A mixture of 2-amino-5-chlorobenzyl alcohol (250 mg, 1.6 mmol) , methyl 2-cyanobenzoate (260mg, 1.6 mmol) and BF3.Et2O (2.5 ml, 48-50% BF3) was heated at 75-80° C under nitrogen atmosphere for 10-12 h. The reaction was monitored by TLC (neat DCM). The reaction mass was quenched in 10% sodium carbonate solution and extracted with DCM (10 x 2 ml). The crude product was purified by column chromatography (using 230-400 mesh silica gel) using dichloromethane (neat) to yield the pure product as a yellowish solid (250 mg, 58% yield).
Author's Comments
The reaction was performed in trifluoroacetic acid (TFA) instead of BF3- Et2O giving 40% yield.
(The reaction is neat reaction where BF3-Et2O or TFA using as solvent.)
Data
1H NMR (CDCl3, 400MHz): 8.046 (1H,d); 7.919 (1H,d); 7.66~ 7.75(2H,m); 7.425 (1H,d); 7.303 (1H,d); 7.17 (1H,s); 4.969 (2H,s)
Mass (M+H): 269.10
Lead Reference
Kshirsagar, U. A.; Argade, N. P. Tetrahedron, 2009, 65, 5244; doi:10.1016/j.tet.2009.04.088
Eguchi, S.; Takeuchi, H., Chem. Comm., 1989, 602; doi:10.1039/C39890000602
Martinez-Viturro, C. M.; Dominguez, D.,Tet. Lett., 2007, 48, 1023; doi:10.1016/j.tetlet.2006.11.168
Kametani, J. Heterocyclic Chem., 1971, 8, 1071; doi:10.1002/jhet.5570080638
Other References
Preparation of Methyl-2-cyano benzoate: Jin, F.; Confalone, P. N. Tet. Lett., 2000, 41, 3271;
doi:10.1016/S0040-4039(00)00384-1Sakamoto, T.; Ohsawa, K., J. Chem Soc., Perkin Trans. 1, 1999, 16, 2323;
doi:10.1039/a903345iSrivastava, R. R.; Zych, A. J.; Jenkins, D. M.; Wang, H.-J.; Chen, Z.-J.; Fairfax, D. J. Synth. Comm., 2007, 37, 431;
doi:10.1080/00397910601039044Chattopadhyay, K.; Dey, R; Ranu, B. C. Tet. Lett., 2009, 50, 3164;
doi:10.1016/j.tetlet.2009.01.027
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Keywords: amines, esters, heterocyclic compounds
