Synthesis of substituted pyrroles from an alkyne, an imine and carbon monoxide via an organotitanium intermediate

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7787-7790

  Gao, Yuan ^a   Shirai, Masaaki ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030597156     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01778-9     Document Type: Article

References (11)

1. 1. Buchwald, S. L.; Wannamaker, M. W.; Watson, B. T. J. Am. Chem. Soc. 1989, 111, 776-777.
2. 2. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206; Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261-4264; Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208-2216.
3. 2. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206; Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261-4264; Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208-2216.
4. 2. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206; Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261-4264; Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208-2216.
5. 3. Gao, Y.; Harada, K.; Sato, F. Tetrahedron Lett.1995, 36, 5913-5916.
6. 4. Gao, Y.; Harada, K.; Sato, F. J. Chem. Soc., Chem. Commun. 1996, 533-534.
7. 5. For insertion of CO into Ti-C bond and its applications in organic synthesis, see: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557-1558; Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818-5819, and references cited therein.
8. 5. For insertion of CO into Ti-C bond and its applications in organic synthesis, see: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557-1558; Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818-5819, and references cited therein.
9. 6. Similar zirconium intermediates corresponding to 5 and 6 were postulated for the reaction of azazirconacyclopentenes with CO by Buchwald, see: reference 1.
10. 4 and concentrated to an oil, which was chromatographed on silica gel to afford N-propyl-2-phenyl-3-hexyl-4-trimethylsilylpyrrole (0.136 g, 71%).
11. 8. For review on the synthesis of pyrroles, see: Katritzky, A. R.; Rees, C. W. Comprehensive Heterocyclic Chemistry; Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon Press: Mew York, 1984, Vol. 4.