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.
Highlights
FunctionalizedIndole skeletons exist as key building blocks in drugs, natural products, pharmaceuticals, alkaloids and agrochemicals and exhibit potent and wide-ranging biological activities [1,2,3,4,5]
The 2-cyanoindole unit is an example of structural motif building blocks and effective precursors for the synthesis of various indole-fused polycycles [13,14,15,16,17,18,19], substituted 2-cyanoindoles [20,21,22,23,24], addition to nitriles [25,26] and indole heterocycle substitution [27,28]
NMDA receptor antagonists E [25] are a class of drugs that work to antagonize or inhibit the action of the N-Methyl-D-aspartate receptor (NMDAR)
Summary
Indole skeletons exist as key building blocks in drugs, natural products, pharmaceuticals, alkaloids and agrochemicals and exhibit potent and wide-ranging biological activities [1,2,3,4,5]. The 2-cyanoindole unit is an example of structural motif building blocks and effective precursors for the synthesis of various indole-fused polycycles [13,14,15,16,17,18,19], substituted 2-cyanoindoles [20,21,22,23,24], addition to nitriles [25,26] and indole heterocycle substitution [27,28] These compounds exhibit a wide range of biological activities (Figure 1). NMDA receptor antagonists E [25] are a class of drugs that work to antagonize or inhibit the action of the N-Methyl-D-aspartate receptor (NMDAR) They are commonly used as anesthetics for animals and humans; the state of anesthesia they induce is referred to as dissociative anesthesia. The cyano group is a valuable and readily available functional group for the preparation of various functional groups such as amines, amides, esters, ketones and their carboxyl derivatives [29]
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