Transition-Metal-Free Reverse Reactivity of (2-Alkynyl)-Arylaldimines: Assembly of Functionalized Amino-Indinones

Kapil Mohan Saini; Rakesh K. Saunthwal; Sushmita; Akhilesh K. Verma

doi:10.1002/chem.201904294

Transition-Metal-Free Reverse Reactivity of (2-Alkynyl)-Arylaldimines: Assembly of Functionalized Amino-Indinones

Kapil Mohan Saini, Rakesh K. Saunthwal, Sushmita, Akhilesh K. Verma^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

10 Citations (Scopus)

Abstract

Transition-metal-free regioselective synthesis of functionalized amino-indenones by the reaction of ortho-alkynylaldehydes with a broad range of primary amines by intramolecular cyclization has been described. The designed reaction proceeds through KOH-mediated Prins-type cyclization and DMSO-promoted oxidation of the cyclopent-2-en-1-one system. The proposed mechanism and role of solvent were well supported by control experiments. For the first time, we have disclosed the reverse reactivity of (2-alkynyl)-arylaldimines in a super basic system.

Original language	English
Pages (from-to)	1017-1021
Number of pages	5
Journal	Chemistry - A European Journal
Volume	26
Issue number	5
DOIs	https://doi.org/10.1002/chem.201904294
Publication status	Published - 16 Jan 2020

Keywords

amino-indinones
ortho-alkynyl aldehyde
primary amines
regioselectivity
transition-metal-free reactions

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title = "Transition-Metal-Free Reverse Reactivity of (2-Alkynyl)-Arylaldimines: Assembly of Functionalized Amino-Indinones",

abstract = "Transition-metal-free regioselective synthesis of functionalized amino-indenones by the reaction of ortho-alkynylaldehydes with a broad range of primary amines by intramolecular cyclization has been described. The designed reaction proceeds through KOH-mediated Prins-type cyclization and DMSO-promoted oxidation of the cyclopent-2-en-1-one system. The proposed mechanism and role of solvent were well supported by control experiments. For the first time, we have disclosed the reverse reactivity of (2-alkynyl)-arylaldimines in a super basic system.",

keywords = "amino-indinones, ortho-alkynyl aldehyde, primary amines, regioselectivity, transition-metal-free reactions",

author = "Saini, {Kapil Mohan} and Saunthwal, {Rakesh K.} and Sushmita and Verma, {Akhilesh K.}",

year = "2020",

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doi = "10.1002/chem.201904294",

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T1 - Transition-Metal-Free Reverse Reactivity of (2-Alkynyl)-Arylaldimines

T2 - Assembly of Functionalized Amino-Indinones

AU - Saini, Kapil Mohan

AU - Saunthwal, Rakesh K.

AU - Sushmita,

AU - Verma, Akhilesh K.

PY - 2020/1/16

Y1 - 2020/1/16

N2 - Transition-metal-free regioselective synthesis of functionalized amino-indenones by the reaction of ortho-alkynylaldehydes with a broad range of primary amines by intramolecular cyclization has been described. The designed reaction proceeds through KOH-mediated Prins-type cyclization and DMSO-promoted oxidation of the cyclopent-2-en-1-one system. The proposed mechanism and role of solvent were well supported by control experiments. For the first time, we have disclosed the reverse reactivity of (2-alkynyl)-arylaldimines in a super basic system.

AB - Transition-metal-free regioselective synthesis of functionalized amino-indenones by the reaction of ortho-alkynylaldehydes with a broad range of primary amines by intramolecular cyclization has been described. The designed reaction proceeds through KOH-mediated Prins-type cyclization and DMSO-promoted oxidation of the cyclopent-2-en-1-one system. The proposed mechanism and role of solvent were well supported by control experiments. For the first time, we have disclosed the reverse reactivity of (2-alkynyl)-arylaldimines in a super basic system.

KW - amino-indinones

KW - ortho-alkynyl aldehyde

KW - primary amines

KW - regioselectivity

KW - transition-metal-free reactions

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DO - 10.1002/chem.201904294

M3 - Article (Academic Journal)

AN - SCOPUS:85078509934

SN - 0947-6539

VL - 26

SP - 1017

EP - 1021

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 5

ER -

Transition-Metal-Free Reverse Reactivity of (2-Alkynyl)-Arylaldimines: Assembly of Functionalized Amino-Indinones

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Keywords

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