Synergistic Cooperative Effect of Sodium borohydride‐Iodine Towards Cascade C−N and C−S/Se Bond Formation: One‐pot Regioselective Synthesis of 3‐Sulfenyl/selenyl Indoles and Mechanistic Insight | Zendy

Lavekar Aditya G. | Zendy; Equbal Danish | Zendy; Sinha Arun K. | Zendy

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Synergistic Cooperative Effect of Sodium borohydride‐Iodine Towards Cascade C−N and C−S/Se Bond Formation: One‐pot Regioselective Synthesis of 3‐Sulfenyl/selenyl Indoles and Mechanistic Insight

Author(s) -

Lavekar Aditya G.,

Equbal Danish,

Sinha Arun K.

Publication year - 2018

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201701028

Subject(s) - chemistry , regioselectivity , sodium borohydride , indole test , nucleophile , combinatorial chemistry , thio , aqueous solution , nucleophilic addition , medicinal chemistry , stereochemistry , organic chemistry , catalysis

In this work, a new strategy to synthesize 3‐sulfenyl/selenyl indole is reported wherein LC−MS reveals a novel insight into synergistic cooperative effect of NaBH 4 ‐I 2 which allows cascade C−N and C−S/C−Se bond formations via reduction‐nucleophilic cyclization‐chalcogenylation, three steps in one‐pot, towards regioselective synthesis of diverse 3‐chalcogenyl indoles including 5‐bromo‐3‐[(3,4,5‐trimethoxyphenyl)thio]‐1H‐indole, a known lead anticancer compound, directly from 2‐amino‐phenacylchlorides and thiophenols or disulfides/diselenides in aqueous dioxane under transition‐metal‐free condition.

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