Synthesis of Free NH 2‐(Aminomethyl)indoles through Copper‐Catalyzed Reaction of 3‐( ortho ‐Trifluoroacetamidophenyl)‐1‐propargylic Alcohols with Amines and Palladium/Copper‐ Cocatalyzed Domino Three‐Component Sonogashira Cross‐Coupling/Cyclization/Substitution Reactions | Zendy

Cacchi Sandro | Zendy; Fabrizi Giancarlo | Zendy; Iazzetti Antonia | Zendy; Molinaro Carmela | Zendy; Verdiglione Rosanna | Zendy; Goggiamani Antonella | Zendy

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Synthesis of Free NH 2‐(Aminomethyl)indoles through Copper‐Catalyzed Reaction of 3‐( ortho ‐Trifluoroacetamidophenyl)‐1‐propargylic Alcohols with Amines and Palladium/Copper‐ Cocatalyzed Domino Three‐Component Sonogashira Cross‐Coupling/Cyclization/Substitution Reactions

Author(s) -

Cacchi Sandro,

Fabrizi Giancarlo,

Iazzetti Antonia,

Molinaro Carmela,

Verdiglione Rosanna,

Goggiamani Antonella

Publication year - 2015

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.201400881

Subject(s) - sonogashira coupling , chemistry , palladium , copper , domino , cascade reaction , catalysis , combinatorial chemistry , organic chemistry , medicinal chemistry

Free NH 2‐(aminomethyl)indoles have been prepared via copper‐catalyzed cyclization of 3‐( ortho ‐trifluoroacetamidophenyl)‐1‐propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficient domino three‐component Sonogashira cross‐coupling/cyclization/substitution process that, omitting the isolation of 3‐( ortho ‐trifluoroacetamidophenyl)‐1‐propargylic alcohols, provides access to this class of compounds by treating 2‐iodotrifluoroacetanilides, propargylic alcohols, and primary or secondary amines with a copper/palladium catalyst system.

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