37714-64-0Relevant academic research and scientific papers
Carbene radicals in cobalt(II)-porphyrin-catalysed carbene carbonylation reactions; A catalytic approach to ketenes
Paul, Nanda D.,Chirila, Andrei,Lu, Hongjian,Zhang, X. Peter,Debruin, Bas
supporting information, p. 12953 - 12958 (2013/10/01)
One-pot radicals: Cobalt(III)-carbene radicals, generated by metallo-radical activation of diazo compounds and N-tosylhydrazone sodium salts with cobalt(II) complexes of porphyrins, readily undergo radical addition to carbon monoxide, allowing the catalytic production of ketenes. These ketenes subsequently react with various amines, alcohols and imines in one-pot tandem transformations to produce differently substituted amides, esters and β-lactams in good isolated yields. Copyright
Synthesis of carbamoylacetates from α-iodoacetate, CO, and amines under Pd/light combined conditions
Sumino, Shuhei,Fusano, Akira,Fukuyama, Takahide,Ryu, Ilhyong
experimental part, p. 1331 - 1334 (2012/07/13)
We developed a novel synthetic method of carbamoylacetates from -iodoacetate, carbon monoxide, and amines under photoirradiation conditions in the presence of a Pd catalyst. This reaction likely proceeds via interplay of radical and organopalladium species. Georg Thieme Verlag Stuttgart · New York.
HETEROCYCLIC COMPOUNDS AND USES THEREOF
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Page/Page column 95, (2012/05/21)
Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.
Pd-catalyzed carbonylation of diazo compounds at atmospheric pressure: A catalytic approach to ketenes
Zhang, Zhenhua,Liu, Yiyang,Ling, Lin,Li, Yuxue,Dong, Yian,Gong, Mingxing,Zhao, Xiaokun,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 4330 - 4341 (2011/06/21)
The carbonylation of carbenes through catalytic cycles is highly desirable due to the importance of ketene-mediated reactions in organic synthesis. In this investigation, a highly efficient and mild catalytic approach toward ketene intermediates has been developed based on Pd-catalyzed carbonylation of diazo compounds with CO. When α-diazocarbonyl compounds or N-tosylhydrazone salts are heated in the presence of a palladium catalyst under atmospheric pressure of CO, ketene intermediates are formed in situ, where they undergo further reactions with various nucleophiles such as alcohols, amines, or imines. The Pd-catalyzed tandem carbonylation-Staudinger cycloaddition gives β-lactam derivatives in good yields with excellent trans diastereoselectivity. The results from DFT calculation on the reaction mechanism suggest that Pd is involved in the [2 + 2] cycloaddition process and affects the diastereoselectivity of the β-lactam products by assisting isomerization of the addition intermediate. On the other hand, the acylketenes generated from the Pd-catalyzed carbonylation of α-diazoketones react with imines in a formal [4 + 2] cycloaddition manner to afford 1,3-dioxin-4-one derivatives. This straightforward carbonylation provides a new approach toward highly efficient catalytic generation of ketene species under mild conditions.
Nucleophilic substitution accompanying carbon-carbon bond cleavage assisted by a nitro group
Nakaike, Yumi,Taba, Noriko,Itoh, Shinobu,Tobe, Yoshito,Nishiwaki, Nagatoshi,Ariga, Masahiro
experimental part, p. 2413 - 2417 (2009/09/08)
A 2-nitrated 3-oxoester reacted with amines or alcohols to afford unsymmetrical malonic acid derivatives as a result of nucleophilic substitution accompanying C-C bond cleavage. The 2-nitrated 3-oxoester easily formed ammonium salts with amines. When the amine is liberated from the salt under equilibrium, nucleophilic amine and electrophilic keto ester locate close to each other. This intimate pair effect causes a pseudo intramolecular reaction to occur, giving rise to effective substitution under mild conditions.
New indium-mediated cyclisation reactions of tethered haloenynes in aqueous solvent systems
Goeta, Andres,Salter, Matthew M.,Shah, Hummad
, p. 3582 - 3599 (2007/10/03)
The intramolecular cyclisation of tethered allyl bromides onto terminal alkynes mediated by metallic indium proceeds smoothly and cleanly in mixtures of THF and H2O to give unsaturated carbocycles and heterocycles in good yield. Alternatively, the cyclisation may be carried out in anhydrous THF with the aid of acid catalysis. The reaction is also mediated by a range of indium salts and proceeds with substoichiometric quantities of indium in the presence of a co-reductant. Deuteration studies show that the reaction proceeds via a concerted syn carboindination of the carbon-carbon triple bond to give an intermediate, which is protonated in situ.
Studies on the Chemistry of O,N- and S,N-Containing Heterocycles, 8. - Synthesis and Reactivity of 1,5-Benzoxazepine-2,4(3H,5H)-dione
Bartsch, Herbert,Erker, Thomas
, p. 177 - 180 (2007/10/02)
The title compound 4 is synthesized by reaction of 2-aminophenol (1) with the thioester 2.The physico-chemical and spectroscopical data are different from a product with the same formula which has been published recently.The structure of our compound is confirmed by their chemical behaviour, too.Thionation of 4 leads to 5, which can be methylated to 8.Thiolactam 5 reacts with ethyl bromoacetate to yield benzoxazole 6 or benzoxazepine 7, dependent on the base used.From thiolactim 8 compound 10 is obtained with morpholine.The mechanism of the ring contraction is discussed.
Enamines; 44. 2-Acyl-1,1-diamino-ethenes. A New Source of Methylketones, β-Keto Amides and β-Keto Esters
Armati, Antonella,Ruggieri, Pietro De,Rossi, Elisabetta,Stradi, Riccardo
, p. 573 - 576 (2007/10/02)
A general synthesis of 2-acyl-1,1-diamino-ethenes by reaction of 1,1-dimorpholino- and 1,1-dipiperidino-ethenes with aliphatic and aromatic acyl chlorides and their utilization as a source of methylketones, β-keto amides and β-keto esters is reported.
1,2-Dithiol-3-ylideneammonium derivatives, compositions and use
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, (2008/06/13)
New compounds of the formula: STR1 wherein X? is an anion, R is (C1-7) alkyl [unsubstituted or substituted by hydroxy, carboxy, alkoxycarbonyl, cyano, dialkylamino, alkylcarbonyl, or benzoyl which is unsubstituted or substituted by o
