The PdCl2-catalyzed sequential heterocyclization/Michael addition cascade in the synthesis of 2,3-disubstituted indoles

Donala Janreddy; Veerababurao Kavala; Chun Wei Kuo; Ting Shen Kuo; Chiu Hui He; Ching Fa Yao

doi:10.1016/j.tet.2013.01.081

The PdCl₂-catalyzed sequential heterocyclization/Michael addition cascade in the synthesis of 2,3-disubstituted indoles

Donala Janreddy, Veerababurao Kavala, Chun Wei Kuo, Ting Shen Kuo, Chiu Hui He, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

Abstract

A cascade reaction of 2-N-unprotected-2-alkynylanilines and various electron-deficient alkenes in the presence of PdCl₂ provided 2,3-disubstituted indole derivatives, whereas, in the presence of Pd(OAc) ₂, the same reaction resulted in the production of N-alkylated-2-alkynylaniline derivatives.

Original language	English
Pages (from-to)	3323-3330
Number of pages	8
Journal	Tetrahedron
Volume	69
Issue number	15
DOIs	https://doi.org/10.1016/j.tet.2013.01.081
Publication status	Published - 2013 Apr 15

Keywords

2,3-Disubstituted indoles
2-Alkynylanilines
Cascade reaction
PdCl
α,β-Unsaturated ketones

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2013.01.081

Cite this

@article{0fc93b1671454360b1283e9b9b32e4f1,

title = "The PdCl2-catalyzed sequential heterocyclization/Michael addition cascade in the synthesis of 2,3-disubstituted indoles",

abstract = "A cascade reaction of 2-N-unprotected-2-alkynylanilines and various electron-deficient alkenes in the presence of PdCl2 provided 2,3-disubstituted indole derivatives, whereas, in the presence of Pd(OAc) 2, the same reaction resulted in the production of N-alkylated-2-alkynylaniline derivatives.",

keywords = "2,3-Disubstituted indoles, 2-Alkynylanilines, Cascade reaction, PdCl, α,β-Unsaturated ketones",

author = "Donala Janreddy and Veerababurao Kavala and Kuo, {Chun Wei} and Kuo, {Ting Shen} and He, {Chiu Hui} and Yao, {Ching Fa}",

note = "Funding Information: Financial support for this work by the National Science Council of the Republic of China ( NSC 99-2119-M-003-003-MY2 ) and National Taiwan Normal University ( 99T3030-2 , 99-D , 100-D-06 ) is gratefully acknowledged. ",

year = "2013",

month = apr,

day = "15",

doi = "10.1016/j.tet.2013.01.081",

language = "English",

volume = "69",

pages = "3323--3330",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "15",

}

TY - JOUR

T1 - The PdCl2-catalyzed sequential heterocyclization/Michael addition cascade in the synthesis of 2,3-disubstituted indoles

AU - Janreddy, Donala

AU - Kavala, Veerababurao

AU - Kuo, Chun Wei

AU - Kuo, Ting Shen

AU - He, Chiu Hui

AU - Yao, Ching Fa

N1 - Funding Information: Financial support for this work by the National Science Council of the Republic of China ( NSC 99-2119-M-003-003-MY2 ) and National Taiwan Normal University ( 99T3030-2 , 99-D , 100-D-06 ) is gratefully acknowledged.

PY - 2013/4/15

Y1 - 2013/4/15

N2 - A cascade reaction of 2-N-unprotected-2-alkynylanilines and various electron-deficient alkenes in the presence of PdCl2 provided 2,3-disubstituted indole derivatives, whereas, in the presence of Pd(OAc) 2, the same reaction resulted in the production of N-alkylated-2-alkynylaniline derivatives.

AB - A cascade reaction of 2-N-unprotected-2-alkynylanilines and various electron-deficient alkenes in the presence of PdCl2 provided 2,3-disubstituted indole derivatives, whereas, in the presence of Pd(OAc) 2, the same reaction resulted in the production of N-alkylated-2-alkynylaniline derivatives.

KW - 2,3-Disubstituted indoles

KW - 2-Alkynylanilines

KW - Cascade reaction

KW - PdCl

KW - α,β-Unsaturated ketones

UR - http://www.scopus.com/inward/record.url?scp=84875226499&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84875226499&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2013.01.081

DO - 10.1016/j.tet.2013.01.081

M3 - Article

AN - SCOPUS:84875226499

SN - 0040-4020

VL - 69

SP - 3323

EP - 3330

JO - Tetrahedron

JF - Tetrahedron

IS - 15

ER -

The PdCl₂-catalyzed sequential heterocyclization/Michael addition cascade in the synthesis of 2,3-disubstituted indoles

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 857247: Experimental Crystal Structure Determination

Cite this

The PdCl2-catalyzed sequential heterocyclization/Michael addition cascade in the synthesis of 2,3-disubstituted indoles

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 857247: Experimental Crystal Structure Determination

Cite this

The PdCl₂-catalyzed sequential heterocyclization/Michael addition cascade in the synthesis of 2,3-disubstituted indoles