L-proline-catalyzed activation of methyl ketones or active methylene compounds and DMF-DMA for syntheses of (2E)-3-dimethylamino-2- propen-1-ones

Dinesh Kumar; Damodara N. Kommi; Pradeep Chopra; Md Imam Ansari; Asit K. Chakraborti

doi:10.1002/ejoc.201200778

L-proline-catalyzed activation of methyl ketones or active methylene compounds and DMF-DMA for syntheses of (2E)-3-dimethylamino-2- propen-1-ones

Dinesh Kumar, Damodara N. Kommi, Pradeep Chopra, Md Imam Ansari, Asit K. Chakraborti^*

^*Corresponding author for this work

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

36 Citations (Scopus)

Abstract

A cascade organocatalysis is reported for the nucleophilic and electrophilic dual activation taking place in the reaction of methyl ketones or active methylene compounds with DMF-DMA (N,N-dimethylformamide dimethyl acetal). L-Proline serves as an efficient organocatalyst in the covalent and noncovalent synchronous mode for the ambiphilic activation of various aryl, heteroaryl, and styryl methyl ketones, cyclic ketones, and 1,3-diketones with DMF-DMA to achieve the convenient syntheses of the versatile synthons (2E)-1-aryl/ heteroaryl/styryl-3-(dimethylamino)-2-propen-1-ones, (E)-α- [(dimethylamino)formylidene]cycloalkanones, and (E)-2-(dimethylamino) formylidene-1,3-diketones in high yields under solvent-free conditions.

Original language	English
Pages (from-to)	6407-6413
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2012
Issue number	32
DOIs	https://doi.org/10.1002/ejoc.201200778
Publication status	Published - Nov 2012
Externally published	Yes

Keywords

amino acids
domino reactions
hydrogen bonds
organocatalysis
synthetic methods

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title = "L-proline-catalyzed activation of methyl ketones or active methylene compounds and DMF-DMA for syntheses of (2E)-3-dimethylamino-2- propen-1-ones",

abstract = "A cascade organocatalysis is reported for the nucleophilic and electrophilic dual activation taking place in the reaction of methyl ketones or active methylene compounds with DMF-DMA (N,N-dimethylformamide dimethyl acetal). L-Proline serves as an efficient organocatalyst in the covalent and noncovalent synchronous mode for the ambiphilic activation of various aryl, heteroaryl, and styryl methyl ketones, cyclic ketones, and 1,3-diketones with DMF-DMA to achieve the convenient syntheses of the versatile synthons (2E)-1-aryl/ heteroaryl/styryl-3-(dimethylamino)-2-propen-1-ones, (E)-α- [(dimethylamino)formylidene]cycloalkanones, and (E)-2-(dimethylamino) formylidene-1,3-diketones in high yields under solvent-free conditions.",

keywords = "amino acids, domino reactions, hydrogen bonds, organocatalysis, synthetic methods",

author = "Dinesh Kumar and Kommi, {Damodara N.} and Pradeep Chopra and Ansari, {Md Imam} and Chakraborti, {Asit K.}",

year = "2012",

month = nov,

doi = "10.1002/ejoc.201200778",

language = "English",

volume = "2012",

pages = "6407--6413",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Wiley",

number = "32",

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TY - JOUR

T1 - L-proline-catalyzed activation of methyl ketones or active methylene compounds and DMF-DMA for syntheses of (2E)-3-dimethylamino-2- propen-1-ones

AU - Kumar, Dinesh

AU - Kommi, Damodara N.

AU - Chopra, Pradeep

AU - Ansari, Md Imam

AU - Chakraborti, Asit K.

PY - 2012/11

Y1 - 2012/11

N2 - A cascade organocatalysis is reported for the nucleophilic and electrophilic dual activation taking place in the reaction of methyl ketones or active methylene compounds with DMF-DMA (N,N-dimethylformamide dimethyl acetal). L-Proline serves as an efficient organocatalyst in the covalent and noncovalent synchronous mode for the ambiphilic activation of various aryl, heteroaryl, and styryl methyl ketones, cyclic ketones, and 1,3-diketones with DMF-DMA to achieve the convenient syntheses of the versatile synthons (2E)-1-aryl/ heteroaryl/styryl-3-(dimethylamino)-2-propen-1-ones, (E)-α- [(dimethylamino)formylidene]cycloalkanones, and (E)-2-(dimethylamino) formylidene-1,3-diketones in high yields under solvent-free conditions.

AB - A cascade organocatalysis is reported for the nucleophilic and electrophilic dual activation taking place in the reaction of methyl ketones or active methylene compounds with DMF-DMA (N,N-dimethylformamide dimethyl acetal). L-Proline serves as an efficient organocatalyst in the covalent and noncovalent synchronous mode for the ambiphilic activation of various aryl, heteroaryl, and styryl methyl ketones, cyclic ketones, and 1,3-diketones with DMF-DMA to achieve the convenient syntheses of the versatile synthons (2E)-1-aryl/ heteroaryl/styryl-3-(dimethylamino)-2-propen-1-ones, (E)-α- [(dimethylamino)formylidene]cycloalkanones, and (E)-2-(dimethylamino) formylidene-1,3-diketones in high yields under solvent-free conditions.

KW - amino acids

KW - domino reactions

KW - hydrogen bonds

KW - organocatalysis

KW - synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=84868147784&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201200778

DO - 10.1002/ejoc.201200778

M3 - Article

AN - SCOPUS:84868147784

SN - 1434-193X

VL - 2012

SP - 6407

EP - 6413

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 32

ER -

L-proline-catalyzed activation of methyl ketones or active methylene compounds and DMF-DMA for syntheses of (2E)-3-dimethylamino-2- propen-1-ones

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Keywords

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