856782-15-5Relevant academic research and scientific papers
Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3-Chloroindolenines
Saya, Jordy M.,van Wordragen, Ellen D. H.,Orru, Romano V. A.,Ruijter, Eelco
, p. 5156 - 5160 (2019)
C2 allylation of indole derivatives is a challenging but important transformation given the biological relevance of the products. Herein we report a selective C2 allylation strategy that proceeds via allylboration of in situ-generated 3-chloroindolenines. The reaction is mild, practical, and compatible with a wide range of C3-substituted indoles. As allylboronates are readily accessible from commercial precursors, various substituted allyl moieties can be introduced using the same protocol. To showcase the utility of this method we applied it to the synthesis of the natural product, tryprostatin B.
2-Trifluoroacetyl aminoindoles as useful intermediates for the preparation of 2-acylamino indoles
Mangette, John E.,Chen, Xuemei,Krishnamoorthy, Ravi,Samuel Vellekoop,Csakai, Adam J.,Camara, Fatoumata,Paquette, William D.,Wang, Hong-Jun,Takahashi, Hidenori,Fleck, Roman,Roth, Gregory P.
experimental part, p. 1292 - 1295 (2011/04/15)
A three-step method was developed to convert N-1 unprotected 3-substituted indoles to 3-substituted 2-acylaminoindoles. Established indole chlorination chemistry was employed to generate stable 2-trifluoroacetylamino indoles, which were subsequently deprotected and selectively acylated.
