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Volumn 13, Issue 5, 2011, Pages 1261-1263

Three-component strategy toward 5-membered heterocycles from isocyanide dibromides.

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EID: 79952157097     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200003u     Document Type: Article
Times cited : (63)

References (36)
  • 1
    • 26844537872 scopus 로고    scopus 로고
    • For some reviews
    • For some reviews, see: Banfi, L.; Riva, R. Org. React. 2005, 65, 1-140
    • (2005) Org. React. , vol.65 , pp. 1-140
    • Banfi, L.1    Riva, R.2
  • 8
    • 84958690531 scopus 로고
    • 267-335 The Nef isocyanide reaction stands for the formation of imidoyl halides from acyl halides and isocyanides. If one considers the following additions of nucleophilic reagents to form stable adducts such as pyruvamides after water addition, it represents the first (sequential) three-component coupling of isocyanides. For references
    • The Nef isocyanide reaction stands for the formation of imidoyl halides from acyl halides and isocyanides. If one considers the following additions of nucleophilic reagents to form stable adducts such as pyruvamides after water addition, it represents the first (sequential) three-component coupling of isocyanides. For references, see: Nef, J. U. Justus Liebigs Ann. Chem. 1892, 270, 267-335
    • (1892) Justus Liebigs Ann. Chem. , vol.270
    • Nef, J.U.1
  • 22
    • 33847679717 scopus 로고    scopus 로고
    • An isocyanide dihalogenide conversion to chloropyridines followed by a palladium coupling has been reported in a synthesis of variolin analogues. However, with the low yields obtained in the first step, a one-pot multicomponent strategy may be very difficult to settle:;;;,-2601 For an additional cascade involving the cyclization of an isocyanide followed by a Suzuki coupling see:;;;;; Tetrahedron Lett. 2009, 50, 6715-6719
    • An isocyanide dihalogenide conversion to chloropyridines followed by a palladium coupling has been reported in a synthesis of variolin analogues. However, with the low yields obtained in the first step, a one-pot multicomponent strategy may be very difficult to settle: Baeza, A.; Burgos, C.; Alvarez-Builla, J.; Vaquero, J. J. Tetrahedron Lett. 2007, 48, 2597-2601 For an additional cascade involving the cyclization of an isocyanide followed by a Suzuki coupling see: Liu, L.; Wang, Y.; Wang, H.; Peng, C.; Zhao, J.; Zhu, Q. Tetrahedron Lett. 2009, 50, 6715-6719
    • (2007) Tetrahedron Lett. , vol.48 , pp. 2597
    • Baeza, A.1    Burgos, C.2    Alvarez-Builla, J.3    Vaquero, J.J.4    Liu, L.5    Wang, Y.6    Wang, H.7    Peng, C.8    Zhao, J.9    Zhu, Q.10
  • 23
    • 79952179966 scopus 로고
    • For reduction of isocyanide dichloride under pallado-catalyzed Grignard addition
    • For reduction of isocyanide dichloride under pallado-catalyzed Grignard addition see: Ito, Y.; Inouye, M.; Murakami, M. Tetrahedron. Lett. 1988, 29, 181-192
    • (1988) Tetrahedron. Lett. , vol.29 , pp. 181-192
    • Ito, Y.1    Inouye, M.2    Murakami, M.3
  • 29
    • 79952119823 scopus 로고    scopus 로고
    • Without such a cyclization, sequential nucleophilic additions lead to imines prone to hydrolytic cleavage unless engaged in further reactions.
    • Without such a cyclization, sequential nucleophilic additions lead to imines prone to hydrolytic cleavage unless engaged in further reactions.
  • 35
    • 0001060231 scopus 로고
    • Due to the high complexing properties of isocyanides towards transition metals, catalyzed processes are difficult to settle unless using sterically hindered isocyanides:;,-239 For some representative examples see:;; Angew. Chem., Int. Ed. 2000, 39, 4156-4158
    • Due to the high complexing properties of isocyanides towards transition metals, catalyzed processes are difficult to settle unless using sterically hindered isocyanides: Yamamoto, Y.; Yamazaki, H. Coord. Chem. Rev. 1972, 8, 225-239 For some representative examples see: Saluste, C. G.; Whitby, R. J.; Furber, M. Angew. Chem., Int. Ed. 2000, 39, 4156-4158
    • (1972) Coord. Chem. Rev. , vol.8 , pp. 225
    • Yamamoto, Y.1    Yamazaki, H.2    Saluste, C.G.3    Whitby, R.J.4    Furber, M.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.