Tandem one-pot synthesis of flavans by recyclable silica-HClO 4 catalyzed Knoevenagel condensation and [4 + 2]-Diels-Alder cycloaddition

Sandip B. Bharate; Ramesh Mudududdla; Jaideep B. Bharate; Narsaiah Battini; Satyanarayana Battula; Rammohan R. Yadav; Baldev Singh; Ram A. Vishwakarma

doi:10.1039/c2ob25376c

Tandem one-pot synthesis of flavans by recyclable silica-HClO ₄ catalyzed Knoevenagel condensation and [4 + 2]-Diels-Alder cycloaddition

Sandip B. Bharate, Ramesh Mudududdla, Jaideep B. Bharate, Narsaiah Battini, Satyanarayana Battula, Rammohan R. Yadav, Baldev Singh, Ram A. Vishwakarma

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

32 Citations (Scopus)

Abstract

An efficient one-pot multi-component synthesis of flavans using perchloric acid supported on silica as a recyclable heterogeneous catalyst has been described. This is the first report of direct one-step construction of a flavan skeleton from a phenolic precursor. The method involves a Knoevenagel-type condensation leading to in situ formation of transient O-quinone methide which further undergoes [4 + 2]-Diels-Alder cycloaddition with styrene to yield a flavan skeleton. The method provides easy access to a wide range of bio-active natural products viz. flavonoids, anthocyanins and catechins.

Original language	English
Pages (from-to)	5143-5150
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	26
DOIs	https://doi.org/10.1039/c2ob25376c
Publication status	Published - 14 Jul 2012
Externally published	Yes

Access to Document

10.1039/c2ob25376c

Link to publication in Scopus

Cite this

Bharate, Sandip B. ; Mudududdla, Ramesh ; Bharate, Jaideep B. ; Battini, Narsaiah ; Battula, Satyanarayana ; Yadav, Rammohan R. ; Singh, Baldev ; Vishwakarma, Ram A. / Tandem one-pot synthesis of flavans by recyclable silica-HClO ₄ catalyzed Knoevenagel condensation and [4 + 2]-Diels-Alder cycloaddition. In: Organic and Biomolecular Chemistry. 2012 ; Vol. 10, No. 26. pp. 5143-5150.

@article{0097801bf6a547a2b30dc7830502d758,

title = "Tandem one-pot synthesis of flavans by recyclable silica-HClO 4 catalyzed Knoevenagel condensation and [4 + 2]-Diels-Alder cycloaddition",

abstract = "An efficient one-pot multi-component synthesis of flavans using perchloric acid supported on silica as a recyclable heterogeneous catalyst has been described. This is the first report of direct one-step construction of a flavan skeleton from a phenolic precursor. The method involves a Knoevenagel-type condensation leading to in situ formation of transient O-quinone methide which further undergoes [4 + 2]-Diels-Alder cycloaddition with styrene to yield a flavan skeleton. The method provides easy access to a wide range of bio-active natural products viz. flavonoids, anthocyanins and catechins.",

author = "Bharate, {Sandip B.} and Ramesh Mudududdla and Bharate, {Jaideep B.} and Narsaiah Battini and Satyanarayana Battula and Yadav, {Rammohan R.} and Baldev Singh and Vishwakarma, {Ram A.}",

year = "2012",

month = jul,

day = "14",

doi = "10.1039/c2ob25376c",

language = "English",

volume = "10",

pages = "5143--5150",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "The Royal Society of Chemistry",

number = "26",

}

Tandem one-pot synthesis of flavans by recyclable silica-HClO ₄ catalyzed Knoevenagel condensation and [4 + 2]-Diels-Alder cycloaddition. / Bharate, Sandip B.; Mudududdla, Ramesh; Bharate, Jaideep B.; Battini, Narsaiah; Battula, Satyanarayana; Yadav, Rammohan R.; Singh, Baldev; Vishwakarma, Ram A.

In: Organic and Biomolecular Chemistry, Vol. 10, No. 26, 14.07.2012, p. 5143-5150.

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

TY - JOUR

T1 - Tandem one-pot synthesis of flavans by recyclable silica-HClO 4 catalyzed Knoevenagel condensation and [4 + 2]-Diels-Alder cycloaddition

AU - Bharate, Sandip B.

AU - Mudududdla, Ramesh

AU - Bharate, Jaideep B.

AU - Battini, Narsaiah

AU - Battula, Satyanarayana

AU - Yadav, Rammohan R.

AU - Singh, Baldev

AU - Vishwakarma, Ram A.

PY - 2012/7/14

Y1 - 2012/7/14

N2 - An efficient one-pot multi-component synthesis of flavans using perchloric acid supported on silica as a recyclable heterogeneous catalyst has been described. This is the first report of direct one-step construction of a flavan skeleton from a phenolic precursor. The method involves a Knoevenagel-type condensation leading to in situ formation of transient O-quinone methide which further undergoes [4 + 2]-Diels-Alder cycloaddition with styrene to yield a flavan skeleton. The method provides easy access to a wide range of bio-active natural products viz. flavonoids, anthocyanins and catechins.

AB - An efficient one-pot multi-component synthesis of flavans using perchloric acid supported on silica as a recyclable heterogeneous catalyst has been described. This is the first report of direct one-step construction of a flavan skeleton from a phenolic precursor. The method involves a Knoevenagel-type condensation leading to in situ formation of transient O-quinone methide which further undergoes [4 + 2]-Diels-Alder cycloaddition with styrene to yield a flavan skeleton. The method provides easy access to a wide range of bio-active natural products viz. flavonoids, anthocyanins and catechins.

UR - http://www.scopus.com/inward/record.url?scp=84862551060&partnerID=8YFLogxK

U2 - 10.1039/c2ob25376c

DO - 10.1039/c2ob25376c

M3 - Article

C2 - 22648274

AN - SCOPUS:84862551060

VL - 10

SP - 5143

EP - 5150

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 26

ER -