The intramolecular click reaction using 'carbocontiguous' precursors

TETRAHEDRON

卷:73

Article

Patil, Pravin C.¹  Luzzio, Frederick A.¹ 

[1] Univ Louisville, Dept Chem, 2320 South Brook St, Louisville, KY 40292 USA

关键词: Click chemistry;    Cyclic carbohydrates;    Cyclic peptides;    Dipolar cycloaddition;    1,2,3-Triazole;   

DOI  :  10.1016/j.tet.2016.11.016

来源: Elsevier

【 摘 要 】

The synthesis and utilization of all carbon-chain 'carbocontiguous' azidoalkynyl precursors for an intramolecular click reaction is described. The substrates contain both azidoalkyl and ethynylmethyl groups which are conjoined by a 2-(phenylsulfonylmethyl)-4,5-diphenyloxazole lynchpin and are suitably disposed for ring closure. On promotion by copper salts, a number of cyclic click products having the 1,4-disubstituted endo-fused triazole component and the 4,5-diphenyloxazole component are obtained. In one case, removal of the phenylsulfonylmethyl group from the substrate prior to cyclization gave the 1,5-disubstituted exo-fused triazole. The utilization of CuSO4/sodium ascorbate system appears to be the optimal conditions for closure/cyclization and afforded the cyclized products in yields of 84-95%. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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