Tetrahedron

Orthogonal synthesis of pyrroles and 1, 2, 3-triazoles from vinyl azides and 1, 3-dicarbonyl compounds

EPJ Ng, YF Wang, BWQ Hui, G Lapointe, S Chiba

Index: Ng, Eileen Pei Jian; Wang, Yi-Feng; Hui, Benjamin Wei-Qiang; Lapointe, Guillaume; Chiba, Shunsuke Tetrahedron, 2011 , vol. 67, # 40 p. 7728 - 7737

Full Text: HTML

Citation Number: 43

Abstract

Tri-and tetrasubstituted N–H pyrroles were prepared by the simple treatment of vinyl azides with 1, 3-dicarbonyl compounds in toluene at 100° C via 2H-azirine intermediates generated in situ. When the reactions of vinyl azides and 1, 3-dicarbonyl compounds were performed in DMF in the presence of a catalytic amount of K2CO3, 1-vinyl-1, 2, 3-triazoles were obtained via 1, 3-dipolar cycloaddition. These methodologies exploited orthogonal modes of ...

Related Articles:

Infrared heat aided solid state synthesis of pyrroles from 1, 4??diketones and ammonium acetate

[Zhang, Chun; Wang, Jian; Li, Jing-Hua Journal of Heterocyclic Chemistry, 2012 , vol. 49, # 1 p. 204 - 207]

Mn-promoted aerobic oxidative C–C bond cleavage of aldehydes with dioxygen activation: A simple synthetic approach to formamides

[Wang, Yi-Feng; Ton, Kah Kah; Chiba, Shunsuke; Narasaka, Koichi Organic Letters, 2008 , vol. 10, # 21 p. 5019 - 5022]

Ambivalent role of metal chlorides in ring opening reactions of 2H-azirines: synthesis of imidazoles, pyrroles and pyrrolinones

[Auricchio, Sergio; Truscello, Ada M.; Lauria, Mirvana; Meille, Stefano V. Tetrahedron, 2012 , vol. 68, # 36 p. 7441 - 7449]

Cu (OTf) 2-catalyzed synthesis of 2, 3-disubstituted indoles and 2, 4, 5-trisubstituted pyrroles from α-diazoketones

[Reddy, B. V. Subba; Reddy, M. Ramana; Rao, Y. Gopal; Yadav; Sridhar Organic Letters, 2013 , vol. 15, # 3 p. 464 - 467]

Efficient synthesis of pyrroles and 4, 5, 6, 7-tetrahydroindoles via palladium-catalyzed oxidation of hydroxy-enamines

[Aoyagi, Yutaka; Mizusaki, Toshihiko; Shishikura, Masahiro; Komine, Takashi; Yoshinaga, Tokuji; Inaba, Haruko; Ohta, Akihiro; Takeya, Koichi Tetrahedron, 2006 , vol. 62, # 36 p. 8533 - 8538]

More Articles...