Birch reduction of electron-deficient pyrroles

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7664-7665

  Donohoe, Timothy J ^a   Guyo, Paul M ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001570826     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961688u     Document Type: Article

References (17)

1. For general reviews of the Birch reduction see: (a) Mander, L. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Volume 8. (b) Rabideau, P. W.; Marcinow, Z. Org. React. 1992, 42, 1. (c) Rabideau, P. W. Tetrahedron 1989, 45, 1579.
2. For general reviews of the Birch reduction see: (a) Mander, L. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Volume 8. (b) Rabideau, P. W.; Marcinow, Z. Org. React. 1992, 42, 1. (c) Rabideau, P. W. Tetrahedron 1989, 45, 1579.
3. For general reviews of the Birch reduction see: (a) Mander, L. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Volume 8. (b) Rabideau, P. W.; Marcinow, Z. Org. React. 1992, 42, 1. (c) Rabideau, P. W. Tetrahedron 1989, 45, 1579.
4. (a) Siegel, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Volume 8.
5. (b) Gribble, G. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Volume 8.
6. (c) Donohoe, T. J.; Garg R.; Stevenson, C. A. Tetrahedron: Asymmetry 1996, 7, 317.
7. Birch, A. J.; Slobbe, J. Heterocycles 1976, 5, 905.
8. Reduction of the pyrrole nucleus to 3-pyrrolines under acidic conditions is well documented. (a) Evans, G. G. J. Am. Chem. Soc. 1951, 73, 5230. Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076. Cornforth, J.; Du, M. J. Chem. Soc., Perkin Trans. 1 1990, 1463. (b) Ketcha, D. M.; Carpenter, K. P.; Zhou, Q. J. Org. Chem. 1891, 56, 1318. (c) Scott, J. W.; Focella, A.; Hengartner, U. O.; Parrish, D. R.; Valentine, D., Jr. Synth. Commun. 1980, 10, 529. (d) Robertson, A. V.; Witkop, B. J. Am. Chem. Soc. 1962, 84, 1697.
9. Reduction of the pyrrole nucleus to 3-pyrrolines under acidic conditions is well documented. (a) Evans, G. G. J. Am. Chem. Soc. 1951, 73, 5230. Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076. Cornforth, J.; Du, M. J. Chem. Soc., Perkin Trans. 1 1990, 1463. (b) Ketcha, D. M.; Carpenter, K. P.; Zhou, Q. J. Org. Chem. 1891, 56, 1318. (c) Scott, J. W.; Focella, A.; Hengartner, U. O.; Parrish, D. R.; Valentine, D., Jr. Synth. Commun. 1980, 10, 529. (d) Robertson, A. V.; Witkop, B. J. Am. Chem. Soc. 1962, 84, 1697.
10. Reduction of the pyrrole nucleus to 3-pyrrolines under acidic conditions is well documented. (a) Evans, G. G. J. Am. Chem. Soc. 1951, 73, 5230. Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076. Cornforth, J.; Du, M. J. Chem. Soc., Perkin Trans. 1 1990, 1463. (b) Ketcha, D. M.; Carpenter, K. P.; Zhou, Q. J. Org. Chem. 1891, 56, 1318. (c) Scott, J. W.; Focella, A.; Hengartner, U. O.; Parrish, D. R.; Valentine, D., Jr. Synth. Commun. 1980, 10, 529. (d) Robertson, A. V.; Witkop, B. J. Am. Chem. Soc. 1962, 84, 1697.
11. Reduction of the pyrrole nucleus to 3-pyrrolines under acidic conditions is well documented. (a) Evans, G. G. J. Am. Chem. Soc. 1951, 73, 5230. Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076. Cornforth, J.; Du, M. J. Chem. Soc., Perkin Trans. 1 1990, 1463. (b) Ketcha, D. M.; Carpenter, K. P.; Zhou, Q. J. Org. Chem. 1891, 56, 1318. (c) Scott, J. W.; Focella, A.; Hengartner, U. O.; Parrish, D. R.; Valentine, D., Jr. Synth. Commun. 1980, 10, 529. (d) Robertson, A. V.; Witkop, B. J. Am. Chem. Soc. 1962, 84, 1697.
12. Reduction of the pyrrole nucleus to 3-pyrrolines under acidic conditions is well documented. (a) Evans, G. G. J. Am. Chem. Soc. 1951, 73, 5230. Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076. Cornforth, J.; Du, M. J. Chem. Soc., Perkin Trans. 1 1990, 1463. (b) Ketcha, D. M.; Carpenter, K. P.; Zhou, Q. J. Org. Chem. 1891, 56, 1318. (c) Scott, J. W.; Focella, A.; Hengartner, U. O.; Parrish, D. R.; Valentine, D., Jr. Synth. Commun. 1980, 10, 529. (d) Robertson, A. V.; Witkop, B. J. Am. Chem. Soc. 1962, 84, 1697.
13. Reduction of the pyrrole nucleus to 3-pyrrolines under acidic conditions is well documented. (a) Evans, G. G. J. Am. Chem. Soc. 1951, 73, 5230. Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076. Cornforth, J.; Du, M. J. Chem. Soc., Perkin Trans. 1 1990, 1463. (b) Ketcha, D. M.; Carpenter, K. P.; Zhou, Q. J. Org. Chem. 1891, 56, 1318. (c) Scott, J. W.; Focella, A.; Hengartner, U. O.; Parrish, D. R.; Valentine, D., Jr. Synth. Commun. 1980, 10, 529. (d) Robertson, A. V.; Witkop, B. J. Am. Chem. Soc. 1962, 84, 1697.
14. Ding, Z.; Turafiello, J. J. Synth. Commun. 1990, 20, 227.
15. Compound 1 can be prepared conveniently from pyrrole and trichloroacetylchloride: Harbuck, J. W.; Rapoport, H. J. Org. Chem. 1972, 37, 3618.
16. All new compounds have been fully characterized. Compound 6 has been further characterized by X-ray crystallography. Donohoe, T. J.; Guyo, P. M. Unpublished work.
17. See Kaiser, E. M. Synthesis 1972, 391.