TMSCl-catalyzed aza-Diels-Alder reaction: A simple and efficient synthesis of pyrano- and furanoquinolines

Shivaji V. More; M. N.V. Sastry; Ching Fa Yao

doi:10.1055/s-2006-939711

TMSCl-catalyzed aza-Diels-Alder reaction: A simple and efficient synthesis of pyrano- and furanoquinolines

Shivaji V. More
, M. N.V. Sastry
, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

31 Citations (Scopus)

Abstract

An efficient TMSCl-catalyzed synthesis of pyrano- and furanoquinolines and phenanthridinone derivative has been developed. In the presence of TMSCl (20 mol%), various aliphatic, aromatic and heteroaromatic aldehydes reacted with different anilines in the presence of either 2,3-dihydrofuran, 3,4-dihydro-2H-pyran or cyclohexenone to afford the aza-Diels-Alder adducts in excellent yield at room temperature. The ambient conditions, fast reaction rates, and excellent product yields are important characteristics of this reaction.

Original language	English
Pages (from-to)	1399-1403
Number of pages	5
Journal	Synlett
Issue number	9
DOIs	https://doi.org/10.1055/s-2006-939711
Publication status	Published - 2006 Jun 1

Keywords

Excellent yields
One-pot
Pyrano- and furanoquinolines
TMSCl
aza-Diels-Alder reaction

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-2006-939711

Cite this

@article{c1eedbd2cab44d73925257eb0dbf8552,

title = "TMSCl-catalyzed aza-Diels-Alder reaction: A simple and efficient synthesis of pyrano- and furanoquinolines",

abstract = "An efficient TMSCl-catalyzed synthesis of pyrano- and furanoquinolines and phenanthridinone derivative has been developed. In the presence of TMSCl (20 mol\%), various aliphatic, aromatic and heteroaromatic aldehydes reacted with different anilines in the presence of either 2,3-dihydrofuran, 3,4-dihydro-2H-pyran or cyclohexenone to afford the aza-Diels-Alder adducts in excellent yield at room temperature. The ambient conditions, fast reaction rates, and excellent product yields are important characteristics of this reaction.",

keywords = "Excellent yields, One-pot, Pyrano- and furanoquinolines, TMSCl, aza-Diels-Alder reaction",

author = "More, \{Shivaji V.\} and Sastry, \{M. N.V.\} and Yao, \{Ching Fa\}",

year = "2006",

month = jun,

day = "1",

doi = "10.1055/s-2006-939711",

language = "English",

pages = "1399--1403",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "9",

}

TY - JOUR

T1 - TMSCl-catalyzed aza-Diels-Alder reaction

T2 - A simple and efficient synthesis of pyrano- and furanoquinolines

AU - More, Shivaji V.

AU - Sastry, M. N.V.

AU - Yao, Ching Fa

PY - 2006/6/1

Y1 - 2006/6/1

N2 - An efficient TMSCl-catalyzed synthesis of pyrano- and furanoquinolines and phenanthridinone derivative has been developed. In the presence of TMSCl (20 mol%), various aliphatic, aromatic and heteroaromatic aldehydes reacted with different anilines in the presence of either 2,3-dihydrofuran, 3,4-dihydro-2H-pyran or cyclohexenone to afford the aza-Diels-Alder adducts in excellent yield at room temperature. The ambient conditions, fast reaction rates, and excellent product yields are important characteristics of this reaction.

AB - An efficient TMSCl-catalyzed synthesis of pyrano- and furanoquinolines and phenanthridinone derivative has been developed. In the presence of TMSCl (20 mol%), various aliphatic, aromatic and heteroaromatic aldehydes reacted with different anilines in the presence of either 2,3-dihydrofuran, 3,4-dihydro-2H-pyran or cyclohexenone to afford the aza-Diels-Alder adducts in excellent yield at room temperature. The ambient conditions, fast reaction rates, and excellent product yields are important characteristics of this reaction.

KW - Excellent yields

KW - One-pot

KW - Pyrano- and furanoquinolines

KW - TMSCl

KW - aza-Diels-Alder reaction

UR - https://www.scopus.com/pages/publications/33745431146

UR - https://www.scopus.com/pages/publications/33745431146#tab=citedBy

U2 - 10.1055/s-2006-939711

DO - 10.1055/s-2006-939711

M3 - Article

AN - SCOPUS:33745431146

SN - 0936-5214

SP - 1399

EP - 1403

JO - Synlett

JF - Synlett

IS - 9

ER -

TMSCl-catalyzed aza-Diels-Alder reaction: A simple and efficient synthesis of pyrano- and furanoquinolines

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this