AlCl 3 induced C-arylation/cyclization in a single pot: A new route to benzofuran fused N-heterocycles of pharmacological interest

K. Shiva Kumar; Raju Adepu; Ravikumar Kapavarapu; D. Rambabu; G. Rama Krishna; C. Malla Reddy; K. Krishna Priya; Kishore V.L. Parsa; Manojit Pal

doi:10.1016/j.tetlet.2011.12.096

AlCl ₃ induced C-arylation/cyclization in a single pot: A new route to benzofuran fused N-heterocycles of pharmacological interest

K. Shiva Kumar, Raju Adepu, Ravikumar Kapavarapu, D. Rambabu, G. Rama Krishna, C. Malla Reddy, K. Krishna Priya, Kishore V.L. Parsa, Manojit Pal

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

25 Scopus citations

Abstract

A new and one-pot synthesis of benzofuran fused N-heterocycles has been accomplished via AlCl ₃-mediated C-C followed by C-O bond formation between 2,3-dichloropyrazine or its derivatives and phenols. The methodology provided novel compounds as potential inhibitors of PDE4B. The single crystal X-ray data of a synthesized benzofuran derivative are presented. Scope of the methodology, in vitro pharmacological data of some of the synthesized compounds, along with docking study of an active compound are described.

Original language	English
Pages (from-to)	1134-1138
Number of pages	5
Journal	Tetrahedron Letters
Volume	53
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2011.12.096
State	Published - 29 Feb 2012
Externally published	Yes

Keywords

2,3-Dichloropyrazine
AlCl
Benzofuran
PDE4
X-ray

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2011.12.096

Cite this

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title = "AlCl 3 induced C-arylation/cyclization in a single pot: A new route to benzofuran fused N-heterocycles of pharmacological interest",

abstract = "A new and one-pot synthesis of benzofuran fused N-heterocycles has been accomplished via AlCl 3-mediated C-C followed by C-O bond formation between 2,3-dichloropyrazine or its derivatives and phenols. The methodology provided novel compounds as potential inhibitors of PDE4B. The single crystal X-ray data of a synthesized benzofuran derivative are presented. Scope of the methodology, in vitro pharmacological data of some of the synthesized compounds, along with docking study of an active compound are described.",

keywords = "2,3-Dichloropyrazine, AlCl, Benzofuran, PDE4, X-ray",

author = "Kumar, {K. Shiva} and Raju Adepu and Ravikumar Kapavarapu and D. Rambabu and Krishna, {G. Rama} and Reddy, {C. Malla} and Priya, {K. Krishna} and Parsa, {Kishore V.L.} and Manojit Pal",

note = "Funding Information: M.P. and K.P. thank DBT, New Delhi, India for financial support (Grant No. BT/PR12829/Med/30/222/2009 ). K.S. thanks UGC, New Delhi, India for a Dr. D. S. Kothari Post doctoral fellowship [No. F.4-2/2006(BSR)/13-324/2010(BSR)]. R.A. thanks CSIR, New Delhi, India for a Junior Research Fellowship. ",

year = "2012",

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doi = "10.1016/j.tetlet.2011.12.096",

language = "English",

volume = "53",

pages = "1134--1138",

journal = "Tetrahedron Letters",

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T1 - AlCl 3 induced C-arylation/cyclization in a single pot

T2 - A new route to benzofuran fused N-heterocycles of pharmacological interest

AU - Kumar, K. Shiva

AU - Adepu, Raju

AU - Kapavarapu, Ravikumar

AU - Rambabu, D.

AU - Krishna, G. Rama

AU - Reddy, C. Malla

AU - Priya, K. Krishna

AU - Parsa, Kishore V.L.

AU - Pal, Manojit

N1 - Funding Information: M.P. and K.P. thank DBT, New Delhi, India for financial support (Grant No. BT/PR12829/Med/30/222/2009 ). K.S. thanks UGC, New Delhi, India for a Dr. D. S. Kothari Post doctoral fellowship [No. F.4-2/2006(BSR)/13-324/2010(BSR)]. R.A. thanks CSIR, New Delhi, India for a Junior Research Fellowship.

PY - 2012/2/29

Y1 - 2012/2/29

N2 - A new and one-pot synthesis of benzofuran fused N-heterocycles has been accomplished via AlCl 3-mediated C-C followed by C-O bond formation between 2,3-dichloropyrazine or its derivatives and phenols. The methodology provided novel compounds as potential inhibitors of PDE4B. The single crystal X-ray data of a synthesized benzofuran derivative are presented. Scope of the methodology, in vitro pharmacological data of some of the synthesized compounds, along with docking study of an active compound are described.

AB - A new and one-pot synthesis of benzofuran fused N-heterocycles has been accomplished via AlCl 3-mediated C-C followed by C-O bond formation between 2,3-dichloropyrazine or its derivatives and phenols. The methodology provided novel compounds as potential inhibitors of PDE4B. The single crystal X-ray data of a synthesized benzofuran derivative are presented. Scope of the methodology, in vitro pharmacological data of some of the synthesized compounds, along with docking study of an active compound are described.

KW - 2,3-Dichloropyrazine

KW - AlCl

KW - Benzofuran

KW - PDE4

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