6076-12-6Relevant academic research and scientific papers
HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
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Paragraph 0175, (2014/05/24)
Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.
Preparations of 4-substituted 3-carboxypyrazoles
Janin, Yves L.
, p. 1410 - 1414 (2014/01/06)
The scopes of three synthetic methods reported for the preparation of an array of 3-pyrazolecarboxylates featuring substituents on position 4 were investigated. The first one is based on the potassium permanganate oxidation of methylpyrazoles. The second starts with the condensation between DMF dimethylacetal and ethyl pyruvate and is followed by the addition of hydrazine hydrochloride. The last one makes use of the cycloaddition of diazomethane on acrylate esters followed by a bromine-based oxidative rearrangement into 4-substituted 3-pyrazole esters.
A new pyrrole synthesis via silver(I)-catalyzed cycloaddition of vinylogous diazoester and nitrile
Billedeau, Roland J.,Klein, Klara R.,Kaplan, Daniel,Lou, Yan
supporting information, p. 1421 - 1423 (2013/06/26)
A new synthesis of di- and trisubstituted pyrroles was achieved by treating in situ generated vinylogous diazoesters and readily available nitriles with a catalytic amount of silver(I) antimony hexafluoride at room temperature. This method showcased the potential of utilizing silver(I) carbenoids in preparing heterocyclic compounds.
One-pot synthesis of 3(5)-ethoxycarbonylpyrazoles
Martins,Freitag,Flores,Zanatta
, p. 1491 - 1492 (2007/10/02)
A one-pot synthesis of ethoxycarbonylpyrazoles 2a-e, by the cyclocondensation of β-alkoxyvinyl trichloromethyl ketones 1a-e with hydrazine hydrochloride under mild conditions, is reported. A study using compounds 1a-e with different substituents proved that these are versatile building blocks for the synthesis of pyrazole derivatives, having a 3(5)-ethoxycarbonyl substituent, in good yields (70-91%).
Reaction of Carbonyl Compounds with Ethyl Lithiodiazoacetate. Studies Dealing with the Rhodium(II)-Catalyzed Behavior of the Resulting Adducts
Padwa, Albert,Kulkarni, Yashwant S.,Zhang, Zhijia
, p. 4144 - 4153 (2007/10/02)
The carbenoid intermediate derived by treating ethyl 2-diazo-4-phthalimidobutyrate with rhodium(II) octanoate undergoes transannular cyclization onto the adjacent imido carbonyl group.The resulting cyclic carbonyl ylide diploe was trapped with several dipolarophiles.In an attempt to prepare related substrates for cyclization studies, the reaction of ethyl lithiodiazoacetate with various aldehydes and ketones was studied.Treatment of the α-diazo-β-hydroxy ester derived from acetone or cyclopentanone with rhodium(II) octanoate gave rise to a β-keto ester.The exclusive phenyl shift encountered with acetophenone is in keeping with migration to an electron-deficient center.The reaction works well with acrolein, leading to high yields of 3-oxo-4-pentenoate.The 1,2-hydrogen shift pathway was found to proceed much faster than intramolecular cyclopropanation.Dehydration of the α-diazo-β-hydroxy esters generates vinyl diazo esters, which readily cyclize to 1H-pyrazoles on thermolysis.
ETUDE DE CYCLOADDITIONS AUX ALLENES GEM-DIACTIVES PAR DEUX GROUPES ELECTROATTRACTEURS
Danion-Bougot, Renee,Danion, Daniel,Carrie, Robert
, p. 1953 - 1958 (2007/10/02)
Allenes, when they have two electron-withdrawing groups on the same carbon, are closely related to ketenes and can be used as synthetic equivalents of these compounds.Several synthetic approaches are investigated, such as dehydrohalogenation reactions, and an analogue of the Wolff transposition of diazoketones.These allenes undergo readily cycloadditions with imines and diazoalkanes, leading to equivalents of β-lactams and cyclobutanones.
