Benzannulation via the Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles

作者: Tin Yiu Lam , Yu-Pu Wang , Rick L. Danheiser

DOI: 10.1021/JO401635C

关键词:

摘要: A two-stage “tandem strategy” for the synthesis of indoles with a high level substitution on six-membered ring is described. Benzannulation based reaction cyclobutenones ynamides proceeds via cascade four pericyclic reactions to produce multiply substituted aniline derivatives in which position ortho nitrogen can bear wide range functionalized substituents. In second stage tandem strategy, highly are generated acid-, base-, and palladium-catalyzed cyclization annulation processes.

参考文章(79)
José Barluenga, Carlos Valdés, Five‐Membered Heterocycles: Indole and Related Systems ChemInform. ,vol. 43, pp. 377- 531 ,(2011) , 10.1002/9783527637737.CH5
Harry H. Wasserman, Eckehard Dehmlow, Cycloaddition of ketenes to ethoxyacetylene. Tetrahedron Letters. ,vol. 3, pp. 1031- 1034 ,(1962) , 10.1016/S0040-4039(00)70952-X
R. D. Stephens, C. E. Castro, The Substitution of Aryl Iodides with Cuprous Acetylides. A Synthesis of Tolanes and Heterocyclics1 Journal of Organic Chemistry. ,vol. 28, pp. 3313- 3315 ,(1963) , 10.1021/JO01047A008
Yong-Li Zhong, Tony K. M. Shing, Efficient and Facile Glycol Cleavage Oxidation Using Improved Silica Gel-Supported Sodium Metaperiodate. Journal of Organic Chemistry. ,vol. 62, pp. 2622- 2624 ,(1997) , 10.1021/JO9621581
David Brückner, Synthesis of ynamides from formamides Tetrahedron. ,vol. 62, pp. 3809- 3814 ,(2006) , 10.1016/J.TET.2005.11.091
Amos B. Smith, Christopher M. Adams, Sergey A. Kozmin, Daniel V. Paone, Total Synthesis of (−)-Cylindrocyclophanes A and F Exploiting the Reversible Nature of the Olefin Cross Metathesis Reaction Journal of the American Chemical Society. ,vol. 123, pp. 5925- 5937 ,(2001) , 10.1021/JA0106164
Hiroshi Yamanaka, Takao Sakamoto, Yoshinori Kondo, Synthesis of Indole anmd Related Compounds from Halo-nitroaromatics Heterocycles. ,vol. 22, pp. 1347- 1350 ,(1984) , 10.3987/R-1984-06-1347