A Highly Efficient Procedure for 3-Sulfenylation of Indole-2-carboxylates

Abstract

A highly efficient one-pot procedure for 3-sulfenylation of 2-carboxyindoles is described. Treatment of thiols with N-chlorosuccinimide at -78 degrees C in CH(2)Cl(2) affords sulfenyl chlorides in situ that readily react with 2-carboxyindoles to give 3-thioindoles in high yields. This new method is milder, produces less waste, and is compatible with a wide range of thiol and indole functionality. [reaction: see text]

Diaryl and Heteroaryl Sulfides: Synthesis via Sulfenyl Chlorides and Evaluation as Selective Anti-Breast-Cancer Agents

“…Schlosser and co-workers demonstrated reactions of indoles with sulfenyl chlorides prepared in situ. 15 The high reactivity of sulfenyl chlorides allows the reaction to occur at 0 °C. Recently, expansion of the scope of this reaction to include Grignard reagents was reported by Lee and co-workers (Figure 2c).…”

Synthesis of pyrimido[4′,5′:2,3][1,4]thiazepino[7,6-b]quinolines, derivatives of a novel ring system

“…For example, different alkyl derivatives of dihydro-1,4-benzothiazepine are HIV-1 enzyme integrase inhibitor [5] and antitumor agents [6]. Several heteroannulated analogues of this core fragment are also potent inhibitors of herpes simplex virus type 1 replication [7], show antihistamine activity [8], and are vasoconstrictor agents [9]. Various methods for the synthesis of fused 1,4-thiazepine derivatives have been reported in recent years with respect to their different structures [10][11][12][13][14][15][16][17][18].…”

A Base‐Mediated Mild Sulfenylation of Indoles and Pyrrole with α‐Acylthiones

“…The synthetic repertoire leading to 3‐sulfenylindole derivatives is continually being updated, and any new synthetic method that allows the easy insertion of sulfenyl moieties into aza‐aromatics is of particular interest. Due to the nucleophilic nature of indole (and pyrrole) rings, an electrophilic sulfur species is typically used for this purpose, and thiols,5,6 disulfides,7,8 sulfonylhydrazides,9 and quinine mono‐ O , S ‐acetals10 have been used as precursors of the actual sulfur‐transfer reagent. Within this scenario, N ‐alkylthio‐ and N ‐arylthiophthalimides (R‐SNPht, R = Alkyl, Aryl, Pht = Phthaloyl) have been used for a long time as sulfur electrophiles for the formation of new sulfur–sulfur11 and sulfur–nitrogen12 bonds.…”