N-Methylmorpholine and Urotropine as Useful Base Catalysts in Baylis-Hillman Reaction

Palakodety Radha Krishna; Empati Raja Sekhar; V. Kannan

doi:10.1055/s-2004-822320

PAPER

N-Methylmorpholine and Urotropine as Useful Base Catalysts in Baylis-Hillman Reaction [1]

Palakodety Radha Krishna*, Empati Raja Sekhar, V. Kannan
D-206/B, Discovery Laboratory, Organic Chemistry Division-III, Indian Institute of Chemical Technology, Hyderabad-500 007, India
Fax: +91(40)27160387; e-Mail: prkgenius@iict.ap.nic.in, prkgenius@iict.res.in;

Abstract

All articles of this category

Abstract

N-Methylmorpholine and urotropine, inexpensive mild bases, have effectively been utilized as catalysts in Baylis-Hillman reaction to result in good to excellent yields (57-99%) of the products.

Key words

Baylis-Hillman reaction - N-methylmorpholine - urotropine - dioxane-water - base catalyst and activated alkenes

Full Text

References

1

IICT communication NO. 030617.

2 Basavaiah D. Rao PD. Hyma RS. Tetrahedron 1996, 52: 8001

3 Ciganek E. The Morita-Baylis-Hillman reaction, Organic Reactions Vol. 51: Paquette LA. John Wiley & Sons; New York: 1997. p.201

4 Basavaiah D. Rao AJ. Satyanarayana T. Chem. Rev. 2003, 103: 811

5 Leadbeater NE. Pol CVD. J. Chem. Soc., Perkin Trans. 1 2001, 2831

6 Keck GE. Welch DS. Org. Lett. 2002, 4: 3687

7 Roth F. Gygax P. Frater G. Tetrahedron Lett. 1992, 33: 1045

8 Rezgui F. El Gaied MM. Tetrahedron Lett. 1998, 39: 5965

9 Lee KY. Eun Na J. Kim JN. Bull. Kor. Chem. Soc. 2003, 24: 409

10 Aggarwal VK. Mereu A. Chem. Commun. 1999, 2311

11 The Merk Index Vol. 12: Merck and Co. Inc.; NJ, USA: 1996. p.1075

12 Anderson GW. Zimmerman JE. Callahan FM. J. Am. Chem. Soc. 1967, 89: 5012

13 Cox RJ. Jenkins H. Schouten JA. Stentiford RA. Wareing KJ. J. Chem. Soc., Perkin Trans. 1 2000, 2023

14 Karpyak VV. Obushak MD. Ganushchak MI. Molecules 2003, 8: 263

15 Alcaide B. Almendros P. Argoncillo C. J. Org. Chem. 2001, 66: 1612

16 Blazevic N. Kolbah D. Synthesis 1979, 161

17 Bhattacharya A. Segmuller B. Ybarra A. Synth. Commun. 1996, 26: 1775

18 Cai J. Zhou Z. Zhao G. Tang C. Org. Lett. 2002, 4: 4723

19a Radha Krishna P. Kannan V. Ilangovan A. Sharma GVM. Tetrahedron: Asymmetry 2001, 12: 829

19b Radha Krishna P. Kannan V. Sharma GVM. Ramana Rao MHV. Synlett 2003, 888

19c Radha Krishna P. Raja Sekhar E. Kannan V. Tetrahedron Lett. 2003, 44: 4973

19d Radha Krishna P. Kannan V. Sharma GVM. Synth. Commun. 2004, 34: 55

19e Radha Krishna P. Manjuvani A. Kannan V. Sharma GVM. Tetrahedron Lett. 2004, 45: 1183

20 Yu C. Liu B. Hu L. J. Org. Chem. 2001, 66: 5413