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Literature DB >> 14986983

A highly efficient procedure for 3-sulfenylation of indole-2-carboxylates.

Kevin M Schlosser¹, Alexei P Krasutsky, Harriet W Hamilton, Jessica E Reed, Karen Sexton.

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]

Entities: Chemical

Year: 2004 PMID： 14986983 DOI： 10.1021/ol049956v

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

5 in total

1. Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu(4)NI-induced electrophilic cyclization.

Authors: Yu Chen; Chul-Hee Cho; Feng Shi; Richard C Larock
Journal: J Org Chem Date: 2009-09-04 Impact factor: 4.354

5. Diaryl and heteroaryl sulfides: synthesis via sulfenyl chlorides and evaluation as selective anti-breast-cancer agents.

Authors: Ivelina M Yonova; Charlotte A Osborne; Naomi S Morrissette; Elizabeth R Jarvo
Journal: J Org Chem Date: 2014-02-25 Impact factor: 4.354

5 in total

A highly efficient procedure for 3-sulfenylation of indole-2-carboxylates.

1. Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu(4)NI-induced electrophilic cyclization.

2. A novel synthetic route to 3-sulfenyl- and 3-selenylindoles by n-Bu4NI-induced electrophilic cyclization.

3. A new synthesis of S-aryl uracils from aryl thiols and 6-amino uracils in the presence of NCS.

4. I₂-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents.

5. Diaryl and heteroaryl sulfides: synthesis via sulfenyl chlorides and evaluation as selective anti-breast-cancer agents.

A highly efficient procedure for 3-sulfenylation of indole-2-carboxylates.

1. Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu(4)NI-induced electrophilic cyclization.

2. A novel synthetic route to 3-sulfenyl- and 3-selenylindoles by n-Bu4NI-induced electrophilic cyclization.

3. A new synthesis of S-aryl uracils from aryl thiols and 6-amino uracils in the presence of NCS.

4. I2-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents.

5. Diaryl and heteroaryl sulfides: synthesis via sulfenyl chlorides and evaluation as selective anti-breast-cancer agents.

4. I₂-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents.