Selective Hydrolysis of 1-cyanocyclopropane-1-carboxylates: Concise Preparation of 1-carbamoylcyclopropane-1-carboxylates

Abstract

An efficient and straightforward method has been developed for the preparation of 1-carbamoylcyclopropane-1-carboxylate derivatives via selective hydrolysis of 1-cyanocyclopropane-1-carboxylates by using hydroxylamine and sodium acetate system strategy. The structure of 1-carbamoylcyclopropane-1-carboxylate 2a was further confirmed by X-ray single crystal analysis.

Novel copolymers of styrene. 15. Halogen ring-disubstituted propyl 2-cyano-3-phenyl-2-propenoates

“…Similar structure to 2-fluoro-5-methyl PCPP was reported in stereoselective cascade assembling of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid into (1R*,2S*)-1-cyano-5,7dialkyl-4,6,8-trioxo-2-aryl-5,7-diazaspiro [2.5]octane-1-carboxylates [1], as well as in synthesis and application of polysiloxane-supported NAD(P)H model 1-Benzyl-1,4dihydronicotinamide in the reduction of activated olefins [2]. 4-Iodo ring-substituted PCPP was involved in selective hydrolysis of 1-cyanocyclopropane-1-carboxylates leading to concise preparation of 1-carbamoylcyclopropane-1-carboxylates [3], in reaction of indandione with ethyl α-cyano-β-arylacrylates [4], and in base-free Knoevenagel condensation catalyzed by copper metal surfaces [5]. 2-Iodophenyl derivative was used in preparation of 1-carbamoylcyclopropane-1-carboxylates via selective hydrolysis of 1-3 cyanocyclopropane-1-carboxylates [6].…”

“…4-Iodo ring-substituted PCPP was involved in selective hydrolysis of 1-cyanocyclopropane-1-carboxylates leading to concise preparation of 1-carbamoylcyclopropane-1-carboxylates [3], in reaction of indandione with ethyl α-cyano-β-arylacrylates [4], and in base-free Knoevenagel condensation catalyzed by copper metal surfaces [5]. 2-Iodophenyl derivative was used in preparation of 1-carbamoylcyclopropane-1-carboxylates via selective hydrolysis of 1-3 cyanocyclopropane-1-carboxylates [6]. 3,4-Dichloro-ring substituted ethyl ester was used in preparation of a novel Fe3O4@SiO2@propyl@DBU magnetic core-shell nanocatalyst for Knoevenagel reaction in aqueous medium [7], in regio-and stereo-selective synthesis of spiro pyrrolidine and pyrrolizidine derivatives [8], in Knoevenagel condensation using a PEG bridged tertiary amine functionalized ionic liquid exhibiting thermoregulated reversible biphasic behavior with cyclohexane/isopropanol [9], in synthesis of 5,6-dichloroindan-1acids and their tetrazolyl derivatives as analgesic and anti-inflammatory agents [10].…”

Synthesis and styrene copolymerization of dimethyl and dimethoxy ring-substituted 2-methoxyethyl phenylcyanoacrylates

“…3,4-Dimethoxy ring-substituted phenylcyanoacrylate is reported in such applications as K3PO4-promoted cyclopropanation of electron-deficient alkenes with 2-bromo-1,3propanedione compounds [1]; in synthesis of pyranoquinoline derivatives catalyzed by piperidine [2]; in asymmetric reaction of p-quinone diimide via organocatalyzed Michael addition of α-cyanoacetates [3]; in synthesis of substituted ethyl α-cyanocinnamates from 1cyanoacetyl-3,5-dimethylpyrazole [4]; in study of novel polyfunctional pyridines as anticancer and antioxidant agents via synthesis, biological evaluation and in silico ADME-T study [5]; in using of isocyanate-functionalized starch as biorenewable backbone for the preparation and application of poly(ethylene imine) grafted starch [6]; in selective hydrolysis of 1-cyanocyclopropane-1-carboxylates via preparation of 1carbamoylcyclopropane-1-carboxylates [7]; in stereospecific characterization and peripheral modification of 1-(pyrrolidin-1-ylmethyl)-2-[(6-chloro-3-oxo-indan)-formyl]-1,2,3,4tetrahydroisoquinolines as novel selective κ opioid receptor agonists [8]; in synthesis and antiproliferative activity in vitro of new 2-aminobenzimidazole derivatives via reaction of 2arylideneaminobenzimidazole with selected nitriles containing active methylene group [9]; in synthesis of on resin poly(propylene imine) dendrimer and its use as organocatalyst [10]; 3 in a two-step synthesis of selected 1,2,3,4-tetrahydroquinoxaline derivatives from N-aryl-2nitrosoanilines and arylidenecyanoacetic esters [11]; in synthesis and studies of antimicrobial, antiquorum-sensing, antitumor and cytotoxic activities of new series of fused [1,3,4]thiadiazoles [12]; in Trizma as efficient catalyst and reactant in Knoevenagel condensation reaction under conventional heat and microwave irradiation conditions [13]; in using 3-butyl-1-methylimidazolinium borohydride ([BMIM][BH4])-a novel reducing agent for the selective reduction of carbon-carbon double bonds in activated conjugated alkenes [14]; in reaction between ethyl α-cyanocinnamate and o-phenylenediamine following development of an efficient method for the transfer hydrogenation of electronically depleted olefins [15]; in studies on benzo[h]chromenes involving a novel synthesis of benzo[h]chromene and 12-oxa-9,11-diaza-benzo[a]anthracene derivatives as promising antimicrobial agents [16]; in using 7-methyl trimethoprim analogues as inhibitors of the folate metabolizing enzymes [17]; in studies of untifungal activity of 3,4-dimethoxybenzal derivatives [18]; in synth...…”