Michael Addition Initiated Carbocyclization Sequences with Nitroolefins for the Stereoselective Synthesis of Functionalized Heterocyclic and Carbocyclic Systems

Dumez, Estelle; Durand, Anne-Catherine; Guillaume, Mireille; Roger, Pierre-Yves; Faure, Robert; Pons, Jordi; Herbette, Gaëtan; Dulcère, Jean-Pierre; Bonne, Damien; Rodríguez, Jean

doi:10.1002/chem.200901433

Cited by 30 publications

(8 citation statements)

References 241 publications

(109 reference statements)

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“…In other words, acrylamides are privileged reaction partners acting as formal [1,4]-dipoles in the popular aza-Michael initiated ring closure (aza-MIRC) strategy. 52 Examples occupying this category of domino transformations are the subject of this section.…”

Section: Domino Reactions Triggered By An Aza-michael Additionmentioning

confidence: 99%

20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions

Alahyen¹,

Benhamou²,

Dalla³

et al. 2021

Synthesis

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Acrylamides are versatile building blocks easily obtained from readily available starting materials. During the last 20 years, these valuable substrates bearing a nucleophilic nitrogen atom and an electrophilic double bond have proved to be efficient domino partners leading to a wide variety of complex aza-heterocycles of synthetic relevance. In this non-exhaustive review, metal free and metal triggered reactions followed by an annulation will be presented, these two approaches allowing a good modulation of the reactivity of the polyvalent acrylamides.

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Section: Domino Reactions Triggered By An Aza-michael Additionmentioning

confidence: 99%

20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions

Alahyen¹,

Benhamou²,

Dalla³

et al. 2021

Synthesis

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“…In this context, reaction of nitroalkenes 18 and N-methylprop-2-ynyl amine 19 was investigated by Rodriguez et al for the regio-and distereoselective synthesis of the 3-methylenepyrrolidines 20 via Michael addition/5-exo intramolecular nucleophilic carbocyclization cascade (Scheme 6). 22 Kanger et al demonstrated a new asymmetric synthesis of chiral pyrrolidines 22 with three stereocenters from 4-aminocrotonate 21 and nitroolens 15 in the presence of 10 mol% bifunctional thiourea catalyst Cat-2. 23 The selectivity of the reaction is highly dependent on the substituent on the nitrogen atom of the aminocrotonate.…”

Section: Synthesis Of Five-membered Heterocyclesmentioning

confidence: 99%

Part I: Nitroalkenes in the synthesis of heterocyclic compounds

2014

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The applications of nitroalkenes in the synthesis of three-to five-membered O, N and S-heterocycles, including natural products are investigated in this review. These heterocyclic compounds were synthesized from nitroalkenes with a variety of substituents at the a and b-positions and those that were part of common and medium rings via a wide variety of reactions such as Michael addition reactions, epoxidation, [3 + 2] cycloaddition and many cascade/domino/tandem reactions. In addition, the potential of nitroalkenes to take part in multi-component and cascade reactions, particularly, in diastereo-and enantioselective versions is reviewed. The high reactivity of nitroalkenes and their potential to coordinate with the metal catalysts as well as organocatalysts signify them as efficient precursors in synthetic organic chemistry. Also, the flexibility of the nitro group in functional group manipulations has expanded the scope of the nitro group, in general, and nitroalkenes, in particular, in organic synthesis.

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“…The Michael Initiated Ring Closure (MIRC) reaction represents a well-designed approach, which has been used extensively for the construction of carbocyclic compounds 1 and small/medium sized nitrogen 2 or oxygen 3 containing heterocyclic compounds. The MIRC strategy can also be achieved through catalyst free one-pot multicomponent reactions 4 which exhibit high atom-economy and selectivity.…”

Section: Introductionmentioning

confidence: 99%

An efficient catalyst-free synthesis of novel chromeno[4,3-b]quinolones through Michael initiated ring closure (MIRC) reaction with in situ generated 3-(arylmethylene)chroman-2,4-diones

Kumari

Khurana

2017

J Chem Sci

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A catalyst-free multicomponent reaction capable of affording a wide range of eighteen novel chromeno[4,3-b]quinolone derivatives (6a-6r) via one-pot two-step domino protocol, in ethylene glycol is reported. Catalyst-free conditions along with green solvent system make the process eco-friendly as well as economical. High yields of the products were obtained in short reaction times by forming three new bonds and one stereocenter in a single operation. The salient features of the present protocol are short reaction times, eco-friendly solvents, high yields and easy work-up procedure.

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Michael Addition Initiated Carbocyclization Sequences with Nitroolefins for the Stereoselective Synthesis of Functionalized Heterocyclic and Carbocyclic Systems

Cited by 30 publications

References 241 publications

20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions

20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions

Part I: Nitroalkenes in the synthesis of heterocyclic compounds

An efficient catalyst-free synthesis of novel chromeno[4,3-b]quinolones through Michael initiated ring closure (MIRC) reaction with in situ generated 3-(arylmethylene)chroman-2,4-diones

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