14897-67-7Relevant articles and documents
NO donors. Part 16: Investigations on structure-activity relationships of organic mononitrates reveal 2-nitrooxyethylammoniumnitrate as a high potent vasodilator
Koenig, Andreas,Roegler, Carolin,Lange, Kathrin,Daiber, Andreas,Glusa, Erika,Lehmann, Jochen
, p. 5881 - 5885 (2007)
The vasoactive properties of 14 organic mononitrates were investigated in vitro using PGF2α-precontracted porcine pulmonary arteries. A surprisingly wide range of vasorelaxant potencies was observed (pD2: 3.36-7.50). Activities showed to be highly sensitive to the molecular structure and the substituents at the molecular carrier of the nitrate group. A correlation between lipophilicity and vasorelaxant potency could not be recognized. 2-Nitrooxyethylammoniumnitrate (1) was found to be slightly superior to the high potency trinitrate GTN.
Facile Preparation of α-Nitroketones from Enol Silyl Ethers
Rathore, Rajendra,Lin, Zhe,Kochi, Jay K.
, p. 1859 - 1862 (1993)
Treatment of enol silyl ethers with the mild nitrating agent tetranitromethane gives good yields of α-nitroketones at room temperature and below.
Convenient synthesis of 4,5-unsubstituted 3-aroylisoxazoles from methyl aryl ketones and (vinylsulfonyl)benzene in water
Wang, Liang,Tao, Yu,Zhang, Nana,Li, Shubai
, (2021/01/11)
A convenient synthesis of 3-aroylisoxazoles from methyl ketones and (vinylsulfonyl)benzene in 2%TPGS-750-M/H2O has been developed. This reaction proceeds via tandem tert-butyl nitrite-promoted Csp3-H functionalization of methyl ketones, 1,3-dipolar cycloaddition and base-catalyzed aromatization, providing the corresponding products in moderate to good yields.
Enantioselective Addition of α-Nitroesters to Alkynes
Davison, Ryan T.,Parker, Patrick D.,Hou, Xintong,Chung, Crystal P.,Augustine, Sara A.,Dong, Vy M.
supporting information, p. 4599 - 4603 (2021/01/18)
By using Rh–H catalysis, we couple α-nitroesters and alkynes to prepare α-amino-acid precursors. This atom-economical strategy generates two contiguous stereocenters, with high enantio- and diastereocontrol. In this transformation, the alkyne undergoes isomerization to generate a RhIII–π-allyl electrophile, which is trapped by an α-nitroester nucleophile. A subsequent reduction with In powder transforms the allylic α-nitroesters to the corresponding α,α-disubstituted α-amino esters.
Metal-free oxidative nitration of α-carbon of carbonyls leads to one-pot synthesis of thiohydroximic acids from acetophenones
Dighe, Shashikant U.,Mukhopadhyay, Sushobhan,Priyanka, Kumari,Batra, Sanjay
supporting information, p. 4190 - 4193 (2016/09/09)
A metal-free nitration of the α-C-H to carbonyl in propiophenones was achieved with I2/NaNO2 in the presence of an oxidant in dimethyl sulfoxide (DMSO) as the medium. Conversely under similar conditions, reaction of acetophenones produced thiohydroximic acids via a radical-based cascade event which involves oxidative nitration of the α-carbon to a carbonyl followed by Michael addition of the thiomethyl group from DMSO and subsequent rearrangement. Besides DMSO, the scope of the reaction encompasses other symmetrical and unsymmetrical dialkylsulfoxides.
Asymmetric Michael addition of α-nitro-ketones using catalytic peptides
Linton, Brian R.,Reutershan, Michael H.,Aderman, Christopher M.,Richardson, Elizabeth A.,Brownell, Kristen R.,Ashley, Charles W.,Evans, Catherine A.,Miller, Scott J.
, p. 1993 - 1997 (2007/10/03)
Peptide-based catalysts have been developed that promote the asymmetric Michael addition of nitroalkanes. The most effective peptides contain a β-turn structural element as well as a basic histidine and an arylsulfonamide-protected arginine. Excellent yields with enantioselectivities of up to 74% ee have been observed.
Chromate oxidation of α-nitro alcohols to α-nitro ketones: Significant improvements to a classic method
Elmaaty, Tarek Abou,Castle, Lyle W.
, p. 1458 - 1461 (2007/10/03)
A series of eight alkyl and aryl α-nitro ketones were prepared by the potassium dichromate oxidation of the corresponding nitro alcohols. Short reaction times allowed for the easy isolation of pure nitro ketones that are devoid of starting materials and/o
α-nitration of ketones via enol silyl ethers. Radical cations as reactive intermediates in thermal and photochemical processes
Rathore, Rajendra,Kochi, Jay K.
, p. 627 - 639 (2007/10/03)
Highly colored (red) solutions of various enol silyl ethers and tetranitromethane (TNM) are readily bleached to afford good yields of α-nitro ketones in the dark at room temperature or below. Spectral analysis show the red colors to be associated with the intermolecular 1:1 electron donor-acceptor (EDA) complexes between the enol silyl ether and TNM. The formation of similar vividly colored EDA complexes with other electron acceptors (such as chloranil, tetracyanobenzene, tetracyanoquinodimethane, etc.) readily establish enol silyl ethers to be excellent electron donors. The deliberate irradiation of the diagnostic (red) charge-transfer absorption bands of the EDA complexes of enol silyl ethers and TNM at -40 °C affords directly the same α-nitro ketones, under conditions in which the thermal reaction is too slow to compete. A common pathway is discussed in which the electron transfer from the enol silyl ether (ESE) to TNM results in the radical ion triad [ESE?+, NO2?, C(NO2)3-]. A subsequent fast homolytic coupling of the cation radical of the enol silyl ether with NO2? leads to the α-nitro ketones. The use of time-resolved spectroscopy and the disparate behavior of theisomeric enol silyl ethers of α- and β-tetralones as well as of 2-methylcyclohexanone strongly support cation radicals (ESE?+) as the critical intermediate in thermal and photoinduced electron-transfer as described in Schemes 1 and 2, respectively.
A novel one pot synthesis of α-nitroketones from olefins using trimethylsilylnitrate-chromium trioxide reagent system
Reddy, M. Venkat Ram,Kumareswaran,Vankar, Yashwant D.
, p. 7149 - 7152 (2007/10/02)
A variety of α-nitroketones have been obtained from the corresponding olefins in good yields upon reaction with trimethylsilylnitrate-chromium trioxide reagent system.
