59557-05-0Relevant articles and documents
Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds
Hari, Durga Prasad,Schouwey, Lionel,Barber, Verity,Scopelliti, Rosario,Fadaei-Tirani, Farzaneh,Waser, Jerome
supporting information, (2019/05/28)
Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents are now established reagents for the alkynylation of radicals and nucleophiles, yet they present limited possibilities for further structure and reactivity modification. Herein, the first synthesis is reported for the corresponding ethynylbenziodazolone (EBZ) reagents, in which the oxygen atom in the iodoheterocycle is replaced by a nitrogen atom. The substituent on the nitrogen enables further fine-tuning of the reagent structure and reactivity. EBZ reagents are obtained easily from the corresponding benzamides by using a one-step procedure, and display reactivity comparable to that of EBX reagents. In particular, they are applied in an asymmetric copper-catalyzed oxyalkynylation of diazo compounds, which proceeds in high yield and enantioselectivity for a broad range of substituents on the diazo compounds and the alkyne.
Addition of Diazo Compounds ipso -C-H Bond to Carbon Disulfide: Synthesis of 1,2,3-Thiadiazoles under Mild Conditions
Zhang, Lei,Sun, Beiqi,Liu, Qianyi,Mo, Fanyang
supporting information, p. 4275 - 4278 (2018/04/14)
We describe here an operationally simple and straightforward synthesis method for a series of diverse 4,5-disubstituted 1,2,3-thiadiazoles via the nucleophilic addition of α-diazo carbonyl compounds to carbon disulfide. This method features using abundant and inexpensive carbon disulfide under mild reaction conditions.
Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds
Hari, Durga Prasad,Waser, Jerome
supporting information, p. 8420 - 8423 (2017/07/06)
Enantioselective catalytic methods allowing the addition of both a nucleophile and an electrophile onto diazo compounds give a fast access into important building blocks. Herein, we report the highly enantioselective oxyalkynylation of diazo compounds usi
Direct Carboxylation of the Diazo Group ipso-C(sp2)-H bond with Carbon Dioxide: Access to Unsymmetrical Diazomalonates and Derivatives
Liu, Qianyi,Li, Man,Xiong, Rui,Mo, Fanyang
supporting information, p. 6756 - 6759 (2017/12/26)
The direct carboxylation of the ipso-C(sp2)-H bond of a diazo compound with carbon dioxide under mild reaction conditions is described. This method is transition-metal-free, uses a weak base, and proceeds at ambient temperature under atmospheric pressure in carbon dioxide. The carboxylation exhibits high reactivity and is amenable to subsequent diversification. A series of unsymmetrical 1,3-diester/keto/amide diazo compounds are obtained with moderate to excellent yields (up to 99%) with good functional group compatibility.
Diversity-oriented synthesis of quinolines via Friedlaender annulation reaction under mild catalytic conditions
Subhas Bose,Idrees, Mohd,Jakka,Venkateswara Rao
scheme or table, p. 100 - 110 (2010/10/19)
An efficient and practical method has been manifested for the diversity-oriented synthesis of quinolines via Friedlaender annulation reaction for the generation of a wide range of structurally interesting and pharmacologically significant compounds by using eerie ammonium, nitrate as a catalyst (10 mol %) at ambient temperature in 45 min, A variety of functional groups are introduced at various positions of the quinoline moiety, and further the diversity of the core skeleton was expanded at R1 and R 2 positions by the synthesis of various hybrids. Initial screening of the compounds for cytotoxicity against a series of cancer cell lines showed promising results.
(3R)-L-MENTHYL 3-HYDROXYBUTYRATE, PROCESS FOR PRODUCING THE SAME, AND SENSATE COMPOSITION COMPRISING THE SAME
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, (2010/12/29)
The present invention provides a cooling component or sensate component which has further strong cooling intensity and is excellent in the persistency or refresh-feeling and cool-feeling, a sensate composition comprising the same, and various products comprising the sensate composition. The present invention relates to, as a cooling component or sensate component, (3R)-1-menthyl 3-hydroxybutyrate represented by the following formula (I):
Mild and high-yielding synthesis of β-keto esters and β-ketoamides
Sridharan, Vellaisamy,Ruiz, Miriam,Menendez, J. Carlos
experimental part, p. 1053 - 1057 (2010/06/16)
In the presence of sodium acetate, the reaction between 2,2,6-trimethyl-4H-1,3-dioxin-4-one and secondary or tertiary alcohols (including chiral ones) or primary or secondary amines could be carried out in refluxing tetrahydrofuran, under much milder conditions than those described in the literature. In these new conditions, side products normally observed using the traditional protocol were avoided, and-keto esters and-ketoamides were normally obtained in quantitative yields.
PROCESS FOR PRODUCING (3S)-I-MENTHYL 3-HYDROXYBUTYRATE AND SENSATE COMPOSITION
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Page/Page column 8; 9, (2010/12/29)
The present invention provides a cooling component or sensate component which does not have undesirable stimulus feeling, bitterness and the like and is excellent in the persistence of refresh-feeling and cool-feeling, a sensate composition which comprise
Stereoselective formation of a chiral ether by intramolecular O-H insertion reaction of a metal carbenoid generated from diazoacetoacetate
Chun, Young Im,Okuyama, Tadashi,Sugimura, Takashi
, p. 285 - 294 (2008/09/18)
Intermolecular O-H insertion reactions of rhodium carbenoids generated from chiral diazoacetoacetates are less efficient and less stereoselective than the reactions of those generated from the corresponding phenyldiazoacetates. Nevertheless, when the diazoacetoacetate is connected to a phenolic moiety through a 2,4-pentanediol tether, the carbenoid generated shows a high potential in both efficiency and stereoselectivity during the intramolecular O-H insertion reaction to give a cyclic ether in up to 88% diastereomeric excess (de) in quantitative yield. The de value depends on the structure of the tether, but is independent of the catalyst employed. The isomerization of the cyclic ether has been studied under the conditions of equilibrium and kinetic protonation of the corresponding enolate. The similarity between the de values obtained by insertion and those obtained under equilibrium suggests that the rhodium catalyst is eliminated during the early stages of the O-H insertion reaction and that proton transfer, which determines the stereoselectivity, occurs after the elimination of the rhodium metal, independent of the stereochemistry of the initial addition. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Boric acid: an efficient and environmentally benign catalyst for transesterification of ethyl acetoacetate
Kondaiah,Reddy, L. Amarnath,Babu, K. Srihari,Gurav,Huge,Bandichhor,Reddy, P. Pratap,Bhattacharya,Anand, R. Vijaya
, p. 106 - 109 (2008/04/13)
An efficient and environmentally benign boric acid catalyzed protocol for the transesterification of ethyl acetoacetate with a variety of primary and secondary alcohols in good to excellent yields is described. The versatility of this transformation is demonstrated with problematic substrates such as propargyl alcohol and allyl alcohol, which are known to undergo Carroll rearrangement during transesterification.
