A Facile Synthesis of Functionalised 3 H -Pyrroles Promoted by Magnesium and a Catalytic Amount of Iodine †

Abstract

The intermolecular reductive coupling cyclisation of 3,3-diaryl-2-cyanoacrylonitriles or ethyl 3,3-diaryl-2-cyano-acrylates with aromatic nitriles with magnesium and catalytic iodine in THF afforded 3H-pyrroles in good yields under neutral and mild conditions.

Keywords

magnesium acrylonitriles acrylate esters reductive coupling

References

(a) Katritzky

A.R.

, and Lagowski

J. M.

, The Principles of Heterocyclic Chemistry, Academic Press, New York, 1968; (b) M. P. Sammes and A. R. Katritzky, Adv. Heterocycl. Chem. 1982, 32, 233; (c) B. A. Trofimov and A. I. Mikhaleva, Heterocycles, 1994, 37, 1193; (d) M. P. Sammes, Chem. Heterocycl. Compd., 1990, 48(I), 549; (e) A. V. Patel and T. A. Crabb, Rodd's Chem. Carbon Compd. (2nd Ed.), 1997, 4A, 456.

McEwen

W.E.

, Yee

T. T.

, Liao

T. K.

, and Wolf

A. P.

, J. Org. Chem., 1967, 32, 1947.

(a) Cirrincione

, Almerico

A. M.

, Dattolo

, Aiello

, Grimaudo

, Diana

, and Misuraca

, Farmaco, 1992, 47, 1555; (b) G. Cirrincione, A. M. Almerico, S. Grimaudo, P. Diana, F. Mingoia, P. Barraja, and F. Misuraca, Farmaco, 1996, 51, 49.

Wong

J.L.

, and Ritchie

M. H.

, J. C. S. Chem. Commun., 1970, 142.

(a) Leblanc

, Corre

, and Foucaud

, Tetrahedron, 1972, 28, 4039; (b) M. Svilarich-Soenen and A. Foucaud, Tetrahedron, 1972, 28, 5149; (c) S. E. Korostova, S. G. Schevchenko and M. V. Sigalov, Khim. Geterotsikl. Soedin., 1991, 10, 1371; (d) S. E. Korostova, S. G. Schevchenko and V. V. Shcherbakov, Zh. Org. Khim., 1993, 29, 1639.

Firestone

R. A.

, Tetrahedron, 1977, 33, 3009.

(a) McEwen

W.E.

, Berkebile

D. H.

, Liao

T. K.

, and Lin

Y. S.

, J. Org. Chem., 1971, 36, 1459; (b) W. E. McEwen, M. A. Hernandez, C. F. Ling, E. Marmugi, R. M. Padronaggio, C. M. Zepp and J. J. Lubinkowski, J. Org. Chem., 1981, 46, 1656.

For reviews see: (a) Steel

P.G.

, J. Chem. Soc. Perkin Trans. 1, 2001, 2757; (b) A. Krief and A. M. Laval, Chem. Rev., 1999, 99, 745; (c) G. A. Molander, Acc. Chem. Res., 1998, 31, 603; (d) G. A. Molander and C. R. Harris, Tetrahedron, 1998, 54, 3321; (e) G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307; (f) T. Imamota, Lanthanides in Organic Synthesis, Academic Press: London, 1994, Chap. 4; (g) G. A. Molander, Chem Rev, 1992, 92, 29; (h) D. P. Curran, T. L. Fevig, C. P. Jasperse, and M. J. Totleben, Synlett, 1992, 943.

X.L.

, and Zhang

Y. M.

, J. Chem. Soc. Perkin Trans. 1, 2001, 2836.

10.

(a) Lee

G.H.

, Lee

H. K.

, Choi

E. B.

, Kim

B. T.

, and Pak

C. S.

, Tetrahedron Lett., 1995, 36, 5607; (b) G. H. Lee, E. B. Choi, E. Lee and C. S. Pak, J. Org. Chem., 1994, 59, 1428; (c) C. S. Pak, E. Lee and G. H. Lee, J. Org. Chem., 1993, 58, 1523; (d) G. H. Lee, E. B. Choi, E. Lee and C. S. Pak, Tetrahedron Lett., 1993, 34, 4541.

11.

Gorbunov

A.I.

, Monastyrskaya

V. I.

, Ampatsumyan

A. A.

, Klimov

E. S.

, and Okhlobystin

O. Y.

, Zh. Org. Khim. 1991, 27, 2382.

12.

Prajapati

, Borah

H. N.

, Sandhu

J. S.

, and Ghosh

A. C.

, Synth. Commun., 1995, 25, 4025.

13.

(a) Corey

E.J.

, Danheiser

R. L.

, and Chandrasekaran

, J. Org. Chem., 1976, 41, 260. (b) J.-M. Pons, J.-P. Zahra, and M. Santelli, Tetrahedron Lett., 1981, 22, 3965.

14.

(a) Clara

, Gemma

, and Francesc

, J. Organomet. Chem., 2002, 642, 16; (b) L. A. Paquette and S. Usui, Tetrahedron Lett., 1999, 40, 3499; (c) T. Ikeda, S. Yue and C. R. Hutchinson, J. Org. Chem., 1985, 50, 5193.

15.

(a) Coates

R.M.

, and Yee

N. K. N.

, J. Org. Chem., 1992, 57, 4598; (b) E. P. Kündig and A. F. Cunningham, Tetrahedron, 1988, 44, 6855; (c) L. A. Carpino and A. C. Brown, J. Org. Chem. 1985, 50, 1749; (d) M. E. Osborn, J. F. Pegues and L. A. Paquette, J. Org. Chem., 1980, 45, 167; (e) R. O. Hutchins, Suchismita, R. E. Zipkin and I. M. Taffer, Synth. Commun., 1989, 19, 1519.

16.

(a) Yacovan

, and Hoz

, J. Org. Chem., 1997, 62, 771; (b) A. Yacovan, S. Hoz, and I. Bilkis, J. Am. Chem. Soc., 1996, 118, 261; (c) Z. Rapoport, Isr. J. Chem., 1970, 8, 749; (d) J. L. Namy, J. Soupple, and H. B. Kagan, Tetrahedron Lett., 1983, 24, 765; (e) L. H. Zhou and Y. M. Zhang, J. Chem. Soc. Perkin Trans. 1., 1998, 2399. (f) L. H. Zhou, Y. M. Zhang and D. Q. Shi, Tetrahedron Lett., 1998, 39, 8491; (g) L. H. Zhou and Y. M. Zhang, Tetrahedron Lett. 1997, 38, 8063; (h) H. B. Kagan, P. Griard and J. L. Namy, Tetrahedron, 1981, 37 (Suppl 1), 175; (i) H. B. Kagan, New. J. Chem. 1990, 14, 453.

17.

Campaigne

, Bulbenko

G. F.

, Kreighbaum

W. E.

, and Mauloling

D. R.

, J. Org. Chem., 1962, 27, 4428.

18.

Cragoe

E.J.

, Chargles

J. R.

, Robb

, and Sprague

J. M.

, J. Org. Chem., 1950, 15, 381.