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.
(a) KatritzkyA.R., and LagowskiJ. 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.
2.
McEwenW.E., YeeT. T., LiaoT. K., and WolfA. P., J. Org. Chem., 1967, 32, 1947.
3.
(a) CirrincioneG., AlmericoA. M., DattoloG., AielloE., GrimaudoS., DianaP., and MisuracaF., 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.
4.
WongJ.L., and RitchieM. H., J. C. S. Chem. Commun., 1970, 142.
5.
(a) LeblancR., CorreE., and FoucaudA., 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.
6.
FirestoneR. A., Tetrahedron, 1977, 33, 3009.
7.
(a) McEwenW.E., BerkebileD. H., LiaoT. K., and LinY. 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.
8.
For reviews see: (a) SteelP.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.
9.
XuX.L., and ZhangY. M., J. Chem. Soc. Perkin Trans. 1, 2001, 2836.
10.
(a) LeeG.H., LeeH. K., ChoiE. B., KimB. T., and PakC. 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.
GorbunovA.I., MonastyrskayaV. I., AmpatsumyanA. A., KlimovE. S., and OkhlobystinO. Y., Zh. Org. Khim.1991, 27, 2382.
(a) CoreyE.J., DanheiserR. L., and ChandrasekaranS., J. Org. Chem., 1976, 41, 260. (b) J.-M. Pons, J.-P. Zahra, and M. Santelli, Tetrahedron Lett., 1981, 22, 3965.
14.
(a) ClaraV., GemmaB., and FrancescT., 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) CoatesR.M., and YeeN. 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) YacovanA., and HozS., 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.
CampaigneE., BulbenkoG. F., KreighbaumW. E., and MaulolingD. R., J. Org. Chem., 1962, 27, 4428.
18.
CragoeE.J., CharglesJ. R., RobbM., and SpragueJ. M., J. Org. Chem., 1950, 15, 381.
