Tetrahedron

Efficient and simple methods for the introduction of the sulfonyl, acyl and alkyl protecting groups on the nitrogen of indole and its derivatives

O Ottoni, R Cruz, R Alves

Index: Ottoni, Olivia; Cruz, Rosimeire; Alves, Robledo Tetrahedron, 1998 , vol. 54, # 46 p. 13915 - 13928

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Citation Number: 88

Abstract

The benzenesulfonylation, acetylation, methylation and benzylation at the 1 position of indole and its derivatives with bases such as NaOH, KOH and NEt3 are presented. By using weaker bases than the traditional ones (BuLi, NaNH2, etc.), the process is simpler, more general and leads to the products in 80–100% yields. The chemoselectivity in compounds bearing more than one nitrogen is also demonstrated.

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