93290-12-1Relevant articles and documents
Stabilization and activation of unstable propynal in the zeolite nanospace and its application to addition reactions
Hayashi, Daijiro,Igura, Yuta,Masui, Yoichi,Onaka, Makoto
, p. 4422 - 4430 (2017/10/13)
Propynal (HC≡C-CHO), having both a C≡C triple bond and a formyl group in a molecule, is a promising building block but its labile property to easily polymerize often narrows its application for organic synthesis. In a similar way to unstable molecules, such as formaldehyde and acrolein, propynal is also stabilized and remains unchanged in supercages of Na-Y zeolite for over 30 days at ambient temperature. There, the carbonyl oxygen atoms of propynal coordinate to sodium ions in Na-Y which was proved by a 13C-DD/MAS-NMR analysis. In addition, propynal adsorbed in zeolite is sufficiently activated to allow unprecedented reactions; i.e., (1) a 1,3-dipolar cycloaddition with electron-deficient α-diazocarbonyl compounds, (2) a 1,4-addition with mono-, di-, and trimethoxy-substituted benzenes, and (3) a [2 + 2] cycloaddition of unactivated cycloalkenes. The nanospace of the zeolites keeps the products from dimerization during reaction (1) and from successive side-reactions in reaction (2). Quantum chemical calculations demonstrated that reaction (3) proceeds via a one-step-like non-concerted mechanism to afford the corresponding [2 + 2] cycloadducts. These three reactions can produce valuable synthetic intermediates retaining both a formyl group and a C=C double bond.
1,3-dipolar cycloaddition of ethyl diazoacetate to alkynes in the pores of zeolite NaY
Kobayashi, Keijiro,Igura, Yuta,Imachi, Shouhei,Masui, Yoichi,Onaka, Makoto
, p. 60 - 61 (2007/10/03)
Zeolite NaY promotes 1,3-dipolar cycloaddition of ethyl diazoacetate to alkynes having an electron-withdrawing group to afford the corresponding functionalized pyrazoles in high yields. The activation of the dipolarophile inside the pores of NaY is proposed based on the 13CMASNMR analysis. Copyright
1,3-Dipolar cycloaddition in the synthesis of pyrazolyl-substituted nitronyl nitroxides
Tretyakov,Tolstikov,Romanenko,Shvedenkov,Sagdeev,Ovcharenko
, p. 2169 - 2181 (2007/10/03)
A new approach to the synthesis of polyfunctional pyrazolyl-substituted nitronyl nitroxides was developed based on the presynthesized pyrazole derivatives prepared by 1,3-dipolar cycloaddition. The structures of the resulting mono- and biradicals were confirmed by X-ray diffraction.
5-SUBSTITUTED 2H-PYRAZOLE-3-CARBOXYLIC ACID DERIVATIVES AS AGONISTS FOR THE NICOTINIC ACID RECEPTOR RUP25 FOR THE TREATMENT OF DYSLIPIDEMIA AND RELATED DISEASES
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, (2008/06/13)
The present invention relates to certain pyrazole carboxylic acid and ester derivatives, and pharmaceutically acceptable salts thereof, which exhibit useful pharmaceutical properties, for example as agonists for the RUP25 receptor. (I) Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the prophylaxis or treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, insulin resistance, type 2 diabetes, Syndrome-X and the like. In addition, the present invention also provides for the use of the compounds of the invention in combination with other active agents such as those belonging to the class of α -glucosidase inhibitors, aldose reductase inhibitors, biguanides, HMG-CoA reductase inhibitors, squalene synthesis inhibitors, fibrates, LDL catabolism enhancers, angiotensin converting enzyme (ACE) inhibitors, insulin secretion enhancers and the like.the substituents are defined in claim 1.
Substituted pyrazolyl compounds and methods employing such compounds
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, (2008/06/13)
This invention pertains to novel substituted pyrazolyl compounds useful as intravenous anesthetics represented by the Formula: STR1 including geometric and optically active isomeric forms, and the pharmaceutically acceptable acid addition salts thereof, wherein: one of Y and Z is nitrogen, and the other is CH; R1 is hydrogen or lower-alkyl; R2 and R3 are selected from the group consisting of hydrogen, --CHO, lower-alkylcarbonyl, lower-alkoxy carbonyl, lower-alkylaminocarbonyl, lower-alkyl, lower-alkenyl, lower-alkoxy-lower-alkenyl, lower-alkylcarbonyloxymethyl, substituted and unsubstituted heterocyclic rings, and substituted or unsubstituted aryl groups, wherein the symbol * represents a carbon atom which may be asymmetric and at least one of R2 and R3 is other than hydrogen.