A Molecular Electron Density Theory Study of the Synthesis of Spirobipyrazolines through the Domino Reaction of Nitrilimines with Allenoates

A Molecular Electron Density Theory Study of the Synthesis of Spirobipyrazolines through the Domino Reaction of Nitrilimines with Allenoates

The reaction of diphenyl nitrilimine (NI) with methyl 1-methyl-allenoate yielding a spirobipyrazoline has been studied within molecular electron density theory (MEDT) at the MPWB1K/6-311G(d) computational level in dichloromethane. This reaction is a domino process that comprises two consecutive 32CA...

Full description

Bibliographic Details
Main Authors:	Luis R. Domingo, Fatemeh Ghodsi, Mar Ríos-Gutiérrez
Format:	Article
Language:	English
Published:	MDPI AG 2019-11-01
Series:	Molecules
Subjects:	[3+2] cycloaddition reactions nitrilimines allenoates spirobipyrazolines domino reactions molecular electron density theory molecular mechanism
Online Access:	https://www.mdpi.com/1420-3049/24/22/4159

Similar Items

Unveiling the Different Chemical Reactivity of Diphenyl Nitrilimine and Phenyl Nitrile Oxide in [3+2] Cycloaddition Reactions with (R)-Carvone through the Molecular Electron Density Theory
by: Mar Ríos-Gutiérrez, et al.
Published: (2020-02-01)

Synthesis of nitrogen-containing dispiroheterocycles using nitrilimines (II)
by: Dalloul Hany M., et al.
Published: (2010-01-01)

Nucleophilic Trapping Nitrilimine Generated by Photolysis of Diaryltetrazole in Aqueous Phase
by: Yixin Zhang, et al.
Published: (2013-12-01)

Enantioselective [3 + 2] cycloadditions of terminal allenoates with β-sulfonyl-α,β-unsaturated ketones
by: Xiuzheng Li, et al.
Published: (2023-02-01)

Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles
by: Rajesh K. Arigela, et al.
Published: (2013-02-01)

Reaction of Nitrilimines and Nitrile Oxides with Hydrazines, Hydrazones and Oximes
by: Adel M. Awadallah, et al.
Published: (2005-02-01)

Pictet–Spengler-Based Multicomponent Domino Reactions to Construct Polyheterocycles
by: Jun-Duo Hu, et al.
Published: (2023-12-01)

Unveiling the Chemistry of Higher-Order Cycloaddition Reactions within the Molecular Electron Density Theory
by: Luis R. Domingo, et al.
Published: (2022-07-01)

Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles
by: Nerea Conde, et al.
Published: (2022-01-01)

One-Pot Synthesis of 1,3,4-Oxadiazines from Acylhydrazides and Allenoates
by: Su Been Kim, et al.
Published: (2023-04-01)

Review on the recent development on ionic liquid promoted domino reactions in synthesis of eco-compatible and complex molecules
by: Sethuraman Indumathi, et al.
Published: (2023-06-01)

Unveiling the Different Reactivity of Bent and Linear Three-Atom-Components Participating in [3 + 2] Cycloaddition Reactions
by: Mar Ríos-Gutiérrez, et al.
Published: (2021-08-01)

Catalytic multi-step domino and one-pot reactions
by: Svetlana B. Tsogoeva
Published: (2024-02-01)

A Molecular Electron Density Theory Study of the [3+2] Cycloaddition Reaction of <i>Pseudo(mono)radical</i> Azomethine Ylides with Phenyl Vinyl Sulphone
by: Mar Ríos-Gutiérrez, et al.
Published: (2022-06-01)

Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems
by: Alexander F. Khlebnikov, et al.
Published: (2014-04-01)

Enantioselective [3 + 2] annulation of α-substituted allenoates with β,γ-unsaturated N-sulfonylimines catalyzed by a bifunctional dipeptide phosphine
by: Huanzhen Ni, et al.
Published: (2016-02-01)

A mechanochemical domino reaction: From α-methylbenzyl alcohols to diacylfuroxans
by: Li-Yu Lu, et al.
Published: (2022-01-01)

Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions
by: Markus Leibeling, et al.
Published: (2013-10-01)

Domino games and domino puzzles /
by: 410461 Feeflang, K. W. H.
Published: (1975)

Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes
by: M. Emin Cinar, et al.
Published: (2016-04-01)

An efficient synthesis of the guaiane sesquiterpene (−)-isoguaiene by domino metathesis
by: Yuzhou Wang, et al.
Published: (2019-04-01)

Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes
by: Jing Sun, et al.
Published: (2012-10-01)

Alternative Access to Functionalized 2,8-Ethanonoradamantane Derivatives
by: Pelayo Camps, et al.
Published: (2017-05-01)

Recent Advances in the Synthesis of 3,n-Fused Tricyclic Indole Skeletons via Palladium-Catalyzed Domino Reactions
by: Liangxin Fan, et al.
Published: (2023-02-01)

Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis
by: Marie Ruch, et al.
Published: (2020-10-01)

Green Synthesis of Spiro Compounds with Potential Anticancer Activity through Knoevenagel/Michael/Cyclization Multicomponent Domino Reactions Organocatalyzed by Ionic Liquid and Microwave-Assisted
by: Regina Westphal, et al.
Published: (2022-11-01)

On the Mechanism of the Synthesis of Nitrofunctionalised Δ<sup>2</sup>-Pyrazolines via [3+2] Cycloaddition Reactions between α-EWG-Activated Nitroethenes and Nitrylimine TAC Systems
by: Agnieszka Fryźlewicz, et al.
Published: (2022-03-01)

Naphthalenes and Quinolines by Domino Reactions of Morita–Baylis–Hillman Acetates
by: Joel K. Annor-Gyamfi, et al.
Published: (2020-11-01)

Thermally Activable Bistetrazoles for Elastomers Crosslinking
by: Mauro Monti, et al.
Published: (2022-07-01)

Dihydroquinolines, Dihydronaphthyridines and Quinolones by Domino Reactions of Morita-Baylis-Hillman Acetates
by: Joel K. Annor-Gyamfi, et al.
Published: (2021-02-01)

A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones
by: Pitchaimani Prasanna, et al.
Published: (2014-02-01)

Exploring Regio- and Stereoselectivity in [3+2] Cycloaddition: Molecular Electron Density Theory Approach for Novel Spirooxindole-Based Benzimidazole with Pyridine Spacer
by: Saeed Alshahrani, et al.
Published: (2023-07-01)

Unveiling a family of spiro-β-lactams with anti-HIV and antiplasmodial activity via phosphine-catalyzed [3+2] annulation of 6-alkylidene-penicillanates and allenoates
by: Américo J. S. Alves, et al.
Published: (2022-10-01)

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles
by: Timo Lessing, et al.
Published: (2015-12-01)

Baeyer-Villiger-Including Domino Two-Step Oxidations of β-O-Substituted Primary Alcohols: Reflection of the Migratory Aptitudes of O-Substituted Alkyl Group in the Outcome of the Reaction
by: Tom Targel, et al.
Published: (2020-11-01)

Synthesis of Novel <i>N</i>-Heterocyclic Compounds Containing 1,2,3-Triazole Ring System via Domino, “Click” and RDA Reactions
by: Márta Palkó, et al.
Published: (2019-02-01)

A Molecular Electron Density Theory Study of the Competitiveness of Polar Diels–Alder and Polar Alder-ene Reactions
by: Luis R. Domingo, et al.
Published: (2018-07-01)

Domino synthetic strategy for tetrahydrothiophene derivatives from 2-acetylfuran/2-acetylthiophene, benzaldehydes, and sulfur powder
by: Dongdong Chen, et al.
Published: (2022-09-01)

A Molecular Electron Density Theory Study of the Chemoselectivity, Regioselectivity, and Diastereofacial Selectivity in the Synthesis of an Anticancer Spiroisoxazoline derived from α-Santonin
by: Luis R. Domingo, et al.
Published: (2019-02-01)

Reaction of Nitrilimines with 2-Substituted Aza-heterocycles. Synthesis of Pyrrolo[1,2-a]pyridine and Pyrimido[2,1-d]1,2,3,5- tetrazine
by: Jalal A. Zahra, et al.
Published: (2008-01-01)