Palladium-catalyzed regioselective [3 + 2] annulation of internal alkynes and iodo-pyranoquinolines with concomitant ring opening

Trapti Aggarwal; Rajeev R. Jha; Rakesh K. Tiwari; Sonu Kumar; Siva K.Reddy Kotla; Sushil Kumar; Akhilesh K. Verma

doi:10.1021/ol3022935

Palladium-catalyzed regioselective [3 + 2] annulation of internal alkynes and iodo-pyranoquinolines with concomitant ring opening

Trapti Aggarwal, Rajeev R. Jha, Rakesh K. Tiwari, Sonu Kumar, Siva K.Reddy Kotla, Sushil Kumar, Akhilesh K. Verma

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

41 Scopus citations

Abstract

A regioselective tandem synthesis of highly functionalized pyrrolo[1,2-a]quinolines has been developed through a novel strategy by palladium-catalyzed [3 + 2] annulation of iodo-pyranoquinolines and internal alkynes with subsequent ring opening. Pyranoquinoline with n-alkyl substitution at the 3-position leads to the formation of pyrrolo-acridones via [3 + 2] annulations/ring opening and successive intramolecular cross-aldol condensation.

Original language	British English
Pages (from-to)	5184-5187
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	20
DOIs	https://doi.org/10.1021/ol3022935
State	Published - 19 Oct 2012

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title = "Palladium-catalyzed regioselective [3 + 2] annulation of internal alkynes and iodo-pyranoquinolines with concomitant ring opening",

abstract = "A regioselective tandem synthesis of highly functionalized pyrrolo[1,2-a]quinolines has been developed through a novel strategy by palladium-catalyzed [3 + 2] annulation of iodo-pyranoquinolines and internal alkynes with subsequent ring opening. Pyranoquinoline with n-alkyl substitution at the 3-position leads to the formation of pyrrolo-acridones via [3 + 2] annulations/ring opening and successive intramolecular cross-aldol condensation.",

author = "Trapti Aggarwal and Jha, {Rajeev R.} and Tiwari, {Rakesh K.} and Sonu Kumar and Kotla, {Siva K.Reddy} and Sushil Kumar and Verma, {Akhilesh K.}",

year = "2012",

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doi = "10.1021/ol3022935",

language = "British English",

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journal = "Organic Letters",

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T1 - Palladium-catalyzed regioselective [3 + 2] annulation of internal alkynes and iodo-pyranoquinolines with concomitant ring opening

AU - Aggarwal, Trapti

AU - Jha, Rajeev R.

AU - Tiwari, Rakesh K.

AU - Kumar, Sonu

AU - Kotla, Siva K.Reddy

AU - Kumar, Sushil

AU - Verma, Akhilesh K.

PY - 2012/10/19

Y1 - 2012/10/19

N2 - A regioselective tandem synthesis of highly functionalized pyrrolo[1,2-a]quinolines has been developed through a novel strategy by palladium-catalyzed [3 + 2] annulation of iodo-pyranoquinolines and internal alkynes with subsequent ring opening. Pyranoquinoline with n-alkyl substitution at the 3-position leads to the formation of pyrrolo-acridones via [3 + 2] annulations/ring opening and successive intramolecular cross-aldol condensation.

AB - A regioselective tandem synthesis of highly functionalized pyrrolo[1,2-a]quinolines has been developed through a novel strategy by palladium-catalyzed [3 + 2] annulation of iodo-pyranoquinolines and internal alkynes with subsequent ring opening. Pyranoquinoline with n-alkyl substitution at the 3-position leads to the formation of pyrrolo-acridones via [3 + 2] annulations/ring opening and successive intramolecular cross-aldol condensation.

UR - http://www.scopus.com/inward/record.url?scp=84867707661&partnerID=8YFLogxK

U2 - 10.1021/ol3022935

DO - 10.1021/ol3022935

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AN - SCOPUS:84867707661

SN - 1523-7060

VL - 14

SP - 5184

EP - 5187

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Palladium-catalyzed regioselective [3 + 2] annulation of internal alkynes and iodo-pyranoquinolines with concomitant ring opening

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