77094-92-9

Upstream product

• 5256-74-6 1,3-diethyl 2-diazopropanedioate 
• 405-99-2 para-fluorostyrene 
• 790-53-4 diethyl 2-(4-fluorobenzylidene)malonate 
• 1774-47-6 trimethylsulfoxonium iodide 
• 459-57-4 4-fluorobenzaldehyde 
• 685-87-0 Diethyl 2-bromomalonate 
• 15277-68-6 bis(ethoxycarbonyl)(phenyliodinio)methanide 
• 105-53-3 diethyl malonate 

Downstream Products

• 1095968-08-3 diethyl 13-(4-fluorophenyl)-9,10-dihydro-9,10-propanoanthracene-11,11-dicarboxylate 
• 1246536-42-4 1-(ethoxycarbonyl)-2-(4-fluorophenyl)cyclopropanecarboxylic acid 

Relevant academic research and scientific papers

Synthesis of Thio-/Selenopyrrolines via SnCl4-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thio-/Selenocyanates

A straightforward protocol has been developed to access thio-/selenopyrrolines through a (3+2)-cycloaddition of aryl thio-/selenocyanates with donor-acceptor cyclopropanes (DACs) in the presence of SnCl4 as a Lewis acid catalyst. Further, good chemoselectivity was observed when DACs were treated with 3-cyano phenyl thiocyanate. These results suggest that thiocyanate is more reactive than nitrile moiety in such (3+2)-cycloaddition reactions.

Electricity Driven 1,3-Oxohydroxylation of Donor-Acceptor Cyclopropanes: a Mild and Straightforward Access to β-Hydroxy Ketones

An unprecedented external oxidant-free electrochemical protocol for 1, 3-oxohydroxylation of donor-acceptor cyclopropane is disclosed. The strategy encompasses the activation of the labile π-electron cloud of the aryl ring to cleave the strained Csp3?Csp3 bond of cyclopropane to afford the β-hydroxy ketones via insertion of molecular oxygen. More significantly, based on the detailed mechanistic investigations and cyclic voltammetry experiments, a plausible mechanism is proposed.

Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine

A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.

[3+3] Annulation via Ring Opening/Cyclization of Donor–Acceptor Cyclopropanes with (Un)symmetrical Ureas: A Quick Access to Highly Functionalized Tetrahydropyrimidinones

A mild and straight-forward access to pharmacologically privileged tetrahydropyrimidinones exploiting readily available Donor–Acceptor cyclopropanes (DACs) is reported. This methodology involves the Lewis acid catalyzed synthesis of uriedo-malonates from (un)symmetrical ureas and DACs followed by I2-base mediated cyclization to their corresponding tetrahydropyrimidinones. The cyclization protocol involves nucleophilic attack of the nitrogen of urea on the newly generated electrophilic acceptor end of DAC. The post functionalization offered potential biologically active molecules.

A practical and reusable catalyst for the synthesis of donor-acceptor cyclopropane

Herein, a convenient, recyclable and inexpensive Cu-based catalytic system is developed for the synthesis of donor-acceptor (D-A) cyclopropane via the cycloaddition of styrene derivatives with diethyl bromomalonate. A core-shell catalyst of Fe3

Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2- b]pyridazines

In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor-acceptor cyclopropanes to furnish hexahydropyrrolo[1,2-b]pyridazines. We also performed these two steps in one pot in a consecutive manner. In addition, a monodecarboxylation reaction of hexahydropyrrolo[1,2-b]pyridazine was achieved with a good yield.

Synthesis of Indenopyridine Derivatives via MgI2-Promoted [2+4] Cycloaddition Reaction of In-situ Generated 2-Styrylmalonate from Donor-Acceptor Cyclopropanes and Chalconimines

An unexpected MgI2-promoted [2+4] cycloaddition reaction of in-situ generated 2-styrylmalonate from donor-acceptor cyclopropanes with chalconimines to synthesize highly substituted indenopyridine derivatives under the mild reaction conditions h

Sc(OTf)3-Catalyzed [3 + 3] Cycloaddition of Cyclopropane 1,1-Diesters with Phthalazinium Dicyanomethanides

The Sc(OTf)3-catalyzed diastereoselective [3 + 3] cycloaddition of phthalazinium dicyanomethanides with cyclopropane 1,1-diesters proceeded smoothly under mild reaction conditions, affording a variety of 3,4-dihydro-1H-pyrido[2,1-a]phthalazine derivatives in up to 99% yields with excellent diastereoselectivities.

Synthesis and anticonvulsant activity of new 6-methyl-1-substituted-4,6- diazaspiro[2.4]heptane-5,7-diones

In the present study on the development of new anticonvulsants, twenty new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones were synthesized and tested for anticonvulsant activity using the maximal electroshock (MES) and subcutaneous pentylene

Rhodium-catalyzed cyclopropanation of alkenes with dimethyl diazomalonate

The outstanding ability of dirhodium α,α,α′, α′-tetramethyl-1,3-benzenedipropanoate [Rh2(esp) 2; esp=α,α,α′,α′-tetramethyl-1,3- benzene-dipropanoate] to catalyze the cyclopropanation of a wide range of alkenes with malonate-derived carbenoids under mild reaction conditions is reported in this communication. The experimental protocol is remarkably simple, uses readily accessible and stable dimethyl diazomalonate with very low catalyst loading. More importantly, the alkene is employed as a limiting reagent.