Synthesis of New Highly Functionalized 1 H-Indole-2-carbonitriles via Cross-Coupling Reactions

Asma Hrizi; Manon Cailler; Moufida Romdhani-Younes; Yvan Carcenac; Jérôme Thibonnet

doi:10.3390/molecules26175287

Synthesis of New Highly Functionalized 1 H-Indole-2-carbonitriles via Cross-Coupling Reactions

Molecules. 2021 Aug 31;26(17):5287. doi: 10.3390/molecules26175287.

Authors

Asma Hrizi^{1

2

3}, Manon Cailler¹, Moufida Romdhani-Younes^{2

3}, Yvan Carcenac¹, Jérôme Thibonnet¹

Affiliations

¹ Laboratoire Synthèse et Isolement de Molécules BioActives EA 7502 SIMBA, Department of Chemistry, Faculté des Sciences et Techniques de Tours, Université de Tours, Parc de Grandmont, 37200 Tours, France.
² Department of Chemistry, Faculté des Sciences de Bizerte, Université de Carthage, Zarzouna, Bizerte 7000, Tunisia.
³ Laboratoire de Chimie (Bio) Organique, Département de Chimie, Faculté des Sciences de Tunis, Campus Universitaire, Université de Tunis El Manar, Structurale et de Polymères-Synthèse et Études Physico-Chimiques (LR99ES14), Tunis 2092, Tunisia.

Abstract

An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki-Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.

Keywords: 1H-indole-2-carbonitriles; Heck; Sonogashira; Stille; Suzuki–Miyaura.