Ca(II)-catalyzed diastereoselective formal [4+2] annulation of a 3-component solvent-free povarov reaction

P. Md Khaja Mohinuddin; Ravikrishna Dada; Abdulrahman I. Almansour; Natarajan Arumugam; Srinivasarao Yaragorla

doi:10.1016/j.tetlet.2019.03.021

Ca(II)-catalyzed diastereoselective formal [4+2] annulation of a 3-component solvent-free povarov reaction

P. Md Khaja Mohinuddin
, Ravikrishna Dada
, Abdulrahman I. Almansour
, Natarajan Arumugam
, Srinivasarao Yaragorla

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

20 Scopus citations

Abstract

Diastereoselective, three-component annulation reaction involving glyoxals, anilines and dienophiles is developed under calcium catalysis. When indene is the dienophile, the reaction gave excellent diastereoselectivity to yield tetrahydro-indenoquinolines, these were further aromatized to get indenoquinolines in one-pot. Aryl acetylenes are used as dienophiles to get 2-acyl quinolines in good yields.

Original language	English (US)
Pages (from-to)	1043-1048
Number of pages	6
Journal	Tetrahedron Letters
Volume	60
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2019.03.021
State	Published - Apr 11 2019
Externally published	Yes

Bibliographical note

Funding Information:
PKM is thankful to CSIR for the fellowship and School of Chemistry, University of Hyderabad, India for the facilities. The authors acknowledge the Deanship of Scientific Research at King Saud University for the Research Grant RG-1440-071 .

Funding Information:
PKM is thankful to CSIR for the fellowship and School of Chemistry, University of Hyderabad, India for the facilities. The authors acknowledge the Deanship of Scientific Research at King Saud University for the Research Grant RG-1440-071.

Publisher Copyright:
© 2019 Elsevier Ltd

Keywords

Annulation reaction
Calcium catalysis
Diastereoselective
Povarov reaction

Publisher link

10.1016/j.tetlet.2019.03.021

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title = "Ca(II)-catalyzed diastereoselective formal [4+2] annulation of a 3-component solvent-free povarov reaction",

abstract = "Diastereoselective, three-component annulation reaction involving glyoxals, anilines and dienophiles is developed under calcium catalysis. When indene is the dienophile, the reaction gave excellent diastereoselectivity to yield tetrahydro-indenoquinolines, these were further aromatized to get indenoquinolines in one-pot. Aryl acetylenes are used as dienophiles to get 2-acyl quinolines in good yields.",

keywords = "Annulation reaction, Calcium catalysis, Diastereoselective, Povarov reaction",

author = "\{Khaja Mohinuddin\}, \{P. Md\} and Ravikrishna Dada and Almansour, \{Abdulrahman I.\} and Natarajan Arumugam and Srinivasarao Yaragorla",

note = "Funding Information: PKM is thankful to CSIR for the fellowship and School of Chemistry, University of Hyderabad, India for the facilities. The authors acknowledge the Deanship of Scientific Research at King Saud University for the Research Grant RG-1440-071 . Funding Information: PKM is thankful to CSIR for the fellowship and School of Chemistry, University of Hyderabad, India for the facilities. The authors acknowledge the Deanship of Scientific Research at King Saud University for the Research Grant RG-1440-071. Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

month = apr,

day = "11",

doi = "10.1016/j.tetlet.2019.03.021",

language = "English (US)",

volume = "60",

pages = "1043--1048",

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TY - JOUR

T1 - Ca(II)-catalyzed diastereoselective formal [4+2] annulation of a 3-component solvent-free povarov reaction

AU - Khaja Mohinuddin, P. Md

AU - Dada, Ravikrishna

AU - Almansour, Abdulrahman I.

AU - Arumugam, Natarajan

AU - Yaragorla, Srinivasarao

N1 - Funding Information: PKM is thankful to CSIR for the fellowship and School of Chemistry, University of Hyderabad, India for the facilities. The authors acknowledge the Deanship of Scientific Research at King Saud University for the Research Grant RG-1440-071 . Funding Information: PKM is thankful to CSIR for the fellowship and School of Chemistry, University of Hyderabad, India for the facilities. The authors acknowledge the Deanship of Scientific Research at King Saud University for the Research Grant RG-1440-071. Publisher Copyright: © 2019 Elsevier Ltd

PY - 2019/4/11

Y1 - 2019/4/11

N2 - Diastereoselective, three-component annulation reaction involving glyoxals, anilines and dienophiles is developed under calcium catalysis. When indene is the dienophile, the reaction gave excellent diastereoselectivity to yield tetrahydro-indenoquinolines, these were further aromatized to get indenoquinolines in one-pot. Aryl acetylenes are used as dienophiles to get 2-acyl quinolines in good yields.

AB - Diastereoselective, three-component annulation reaction involving glyoxals, anilines and dienophiles is developed under calcium catalysis. When indene is the dienophile, the reaction gave excellent diastereoselectivity to yield tetrahydro-indenoquinolines, these were further aromatized to get indenoquinolines in one-pot. Aryl acetylenes are used as dienophiles to get 2-acyl quinolines in good yields.

KW - Annulation reaction

KW - Calcium catalysis

KW - Diastereoselective

KW - Povarov reaction

UR - https://www.scopus.com/pages/publications/85062688407

UR - https://www.scopus.com/pages/publications/85062688407#tab=citedBy

U2 - 10.1016/j.tetlet.2019.03.021

DO - 10.1016/j.tetlet.2019.03.021

M3 - Article

AN - SCOPUS:85062688407

SN - 0040-4039

VL - 60

SP - 1043

EP - 1048

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Ca(II)-catalyzed diastereoselective formal [4+2] annulation of a 3-component solvent-free povarov reaction

Abstract

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