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Literature DB >> 21916460

Lewis acid catalyzed direct cyanation of indoles and pyrroles with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS).

Abstract

BF(3)·OEt(2)-catalyzed direct cyanation of indoles and pyrroles using a less toxic, bench-stable, and easily handled electrophilic cyanating agent N-cyano-N-phenyl-para-toluenesulfonamide (NCTS) affords 3-cyanoindoles and 2-cyanopyrroles in good yields with excellent regioselectivity. The substrate scope is broad with respect to indoles and pyrroles.

Entities: Chemical

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Year: 2011 PMID： 21916460 DOI： 10.1021/ol202335p

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

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Cited

10 in total

1. Intramolecular aminocyanation of alkenes by N-CN bond cleavage.

Authors: Zhongda Pan; Sarah M Pound; Naveen R Rondla; Christopher J Douglas
Journal: Angew Chem Int Ed Engl Date: 2014-04-09 Impact factor: 15.336

Review 2. Recent advances in theoretical studies on transition-metal-catalyzed regioselective C-H functionalization of indoles.

Authors: Hongsheng Ma; Tongyan Yu; Longxiao Chi; Cong Huang; Xuwen Li; Rui Zhang; Chao Deng
Journal: J Mol Model Date: 2022-08-22 Impact factor: 2.172

3. One-pot regioselective C-H activation iodination-cyanation of 2,4-diarylquinazolines using malononitrile as a cyano source.

Authors: Ziqiao Yan; Banlai Ouyang; Xunchun Mao; Wei Gao; Zhihong Deng; Yiyuan Peng
Journal: RSC Adv Date: 2019-06-11 Impact factor: 4.036

Lewis acid catalyzed direct cyanation of indoles and pyrroles with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS).

1. Intramolecular aminocyanation of alkenes by N-CN bond cleavage.

Review 2. Recent advances in theoretical studies on transition-metal-catalyzed regioselective C-H functionalization of indoles.

3. One-pot regioselective C-H activation iodination-cyanation of 2,4-diarylquinazolines using malononitrile as a cyano source.

Review 4. Direct cyanation, hydrocyanation, dicyanation and cyanofunctionalization of alkynes.

5. Microwave-assisted synthesis of 3-nitroindoles from N-aryl enamines via intramolecular arene-alkene coupling.

6. Metal-Free Direct C-H Cyanation of Alkenes.

7. Improved Schmidt Conversion of Aldehydes to Nitriles Using Azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-propanol.

Review 8. Recent Advances in Cyanamide Chemistry: Synthesis and Applications.

9. Indole-3-Carbonitriles as DYRK1A Inhibitors by Fragment-Based Drug Design.

10. Synthesis of Various 2-Aminobenzoxazoles: The Study of Cyclization and Smiles Rearrangement.