(Bromodimethyl)sulfonium Bromide Catalyzed One-Pot Synthesis of α-Aminonitriles

Biswanath Das; R. Ramu; B. Ravikanth; K. Ravinder Reddy

doi:10.1055/s-2006-926421

PAPER

(Bromodimethyl)sulfonium Bromide Catalyzed One-Pot Synthesis of α-Aminonitriles [1]

Biswanath Das*, R. Ramu, B. Ravikanth, K. Ravinder Reddy
Organic Chemistry Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)7160512; e-Mail: biswanathdas@yahoo.com;

Abstract

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Abstract

A novel, simple and efficient one-pot synthesis of α-aminonitriles has been achieved by a three-component condensation of carbonyl compounds, amines and trimethylsilyl cyanide in the presence of (bromodimethyl)sulfonium bromide as a catalyst at room temperature. The products were obtained in high yields and in short reaction times.

Keywords

α-aminonitriles - carbonyl compounds - amines - trimethylsilyl cyanide - (bromodimethyl)sulfonium bromide

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References

1

Part 67 in the series ‘Studies on novel synthetic methodologies’; IICT Communication no. 051101.

2a Shafran YM. Bakulev VA. Mokrushin VS. Russ. Chem. Rev. 1989, 58: 148

2b March J. Advanced Organic Chemistry 4th ed.: Wiley; New York: 1999. p.965

3a Weinstock LM. Davis P. Handelsman B. Tull R. J. Org. Chem. 1967, 32: 2823

3b Matier WL. Owens DA. Comer WT. Deitchman D. Ferguson HC. Seidehamel RJ. Young JR. J. Med. Chem. 1973, 16: 901

4a Strecker A. Ann. Chem. Pharm. 1850, 75: 27

4b Groger H. Chem. Rev. 2003, 103: 2795

5a Harusawa S. Hamada Y. Shioiri T. Tetrahedron Lett. 1979, 20: 4663

5b Mai K. Patil G. Tetrahedron Lett. 1984, 25: 4583

5c Kobayashi S. Ishitani H. Chem. Rev. 1999, 99: 1069

6a Ranu BC. Dey SS. Hajra A. Tetrahedron 2002, 58: 2529

6b Yadav JS. Reddy BVS. Easwaraiah B. Srinivas M. Tetrahedron 2004, 60: 1767

6c De SK. Gibbs RA. Tetrahedron Lett. 2004, 45: 7407

6d De SK. Synth. Commun. 2005, 35: 653

6e De SK. Gibbs RA. Synth. Commun. 2005, 35: 961

6f Royer L. De SK. Gibbs RA. Tetrahedron Lett. 2005, 46: 4595

7a Furukawa N. Inoue T. Aida T. Oae S. J. Chem. Soc., Chem. Commun. 1973, 212

7b Olah GA. Yashwant DV. Massoud A. Suryaprakash GA. Synthesis 1979, 720

7c Khan AT. Mondal E. Ghosh S. Islam S. Eur. J. Org. Chem. 2004, 2002 and references therein

7d Kudrimoti S. Bommena VR. Tetrahedron Lett. 2005, 46: 1209

7e Kudrimoti S. Bommena VR. Tetrahedron Lett. 2005, 35: 961

7f Khan AT. Islam S. Majee A. Chattopadhyay T. Ghosh S. J. Mol. Cat. A: Chem. 2005, 239: 158