89332-91-2Relevant academic research and scientific papers
One-Pot Sequential [3 + 3] Dipolar Cycloaddition of Aldehyde or Ketone and Hydroxylamine with Spirocyclopropyl Oxindole
Xu, Peng-Wei,Chen, Chen,Liu, Jia-Kuan,Song, Yu-Ting,Zhou, Feng,Yan, Jun,Zhou, Jian
, p. 12763 - 12774 (2018/10/20)
A Sc(OTf)3-catalyzed highly diastereoselective one-pot sequential [3 + 3] dipolar cycloaddition reaction of aldehyde or ketone, N-alkyl hydroxylamine, and spirocyclopropyl oxindole is developed, allowing facile construction of spirocyclic oxind
(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes
Cordier, Marie,Archambeau, Alexis
supporting information, p. 2265 - 2268 (2018/04/30)
Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route t
A torquoselective extrusion of isoxazoline N-oxides. Application to the synthesis of aryl vinyl and divinyl ketones for Nazarov cyclization
Canterbury, Daniel P.,Herrick, Ildiko R.,Um, Joann,Houk,Frontier, Alison J.
experimental part, p. 3165 - 3179 (2009/09/05)
A mild, convenient reaction sequence for the synthesis of Nazarov cyclization substrates is described. The [3+2] dipolar cycloaddition of a nitrone and an electron-deficient alkyne gives an isolable isoxazoline intermediate, which upon oxidation undergoes stereoselective extrusion of nitrosomethane to give aryl vinyl or divinyl ketones.
Synthesis of functionalized sulfonamides via 1,3-dipolar cycloaddition of pentafluorophenyl vinylsulfonate
Caddick, Stephen,Bush, Hannah D.
, p. 2489 - 2492 (2007/10/03)
(Matrix presented) An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectiv
Studies on chromone derivatives: regioselective 1,3-dipolar and 1,4-cycloaddition reactions of 3-cyano-4H-1-benzopyran-4-thione
Sain, Bir,Prajapati, Dipak,Mahajan, Asha R,Sandhu, Jagir S
, p. 313 - 316 (2007/10/02)
1,3-Dipolar cycloaddition reactions of 3-cyano-4H-1-benzopyran-4-thione 1 with nitrilimines 3, nitrile oxides 7 and aldonitrones 8 yielded regioselective cycloadducts involving the thione function.In the latter two classes, the unstable cycloadducts fragmented to yield 3-cyanochromone 11 and isothiocyanate 12 or thioamide 13, respectively.In contrast, dienamines 14 preferred to react at the carbon-carbon double bond in a 1,4-cycloaddition yielding xanthione (9H-xanthene-9-thione) 16 by elimination of HCN and the amine moiety.Keywords: 1,3-dipolar cycloaddition / 1,4-cycloaddition / 4H-1-benzopyran-4-thione / nitrilimine / nitrile oxide / nitrone
SOME NOVEL ASPECTS OF REGIOSELECTIVITY IN 1,3 DIPOLAR CYCLOADDITIONS OF 4H-1-BENZOPYRAN-4-THIONE
Baruah, Arpan K.,Prajapati, Dipak,Sandhu, Jagir S.
, p. 6137 - 6142 (2007/10/02)
4H-1-Benzopyran-4-thione (1) reacted smoothly with nitrilimines (3a-e) to afford regioselective cycloadducts (4a-e) in good yields.In contrast,benzonitrile oxide (6) and aldonitrones (7a-d) reacted preferentially at the thione function.The unstable cycloadduct (8) or (9) ruptured to give as isolable products chromone (10) and phenyl isothiocyanate (11) and the thioamides (12a-d).This indirectly proves the site of attack of the dipole at the thione group.
Preparation of Vicinal N-Alkylamino Alcohols via Acylation-Rearrangement of Nitrones Followed by Hydride Reduction
Coates, Robert M.,Cummins, Clark H.
, p. 1383 - 1389 (2007/10/02)
Acylation-rearrangement of N-tert-butyl and N-cyclohexyl nitrones of cyclohexanecarboxaldehyde (1), n-butyraldehyde, isobutyraldehyde, 3-cyclohexenecarboxaldehyde, and α-methylpropionaldehyde gave α-pivaloyloxy imines, which underwent reduction with lithi
Utilization of thiocarbonyl transfer reagents. Preparation of thioamides, mercapto esters, and thiapyran derivatives
Harpp, David N.,MacDonald, J. Gavin,Larsen, Charles
, p. 951 - 957 (2007/10/02)
The reaction of 1,1'-thiocarbonyldiimidazole and 1,1'-thiocarbonylbis(1,2,4-triazole) with several aldonitrones has been found to afford thioamides in good yield.Several 1,1'-thiocarbonylbisazoles, which have been shown to undergo Diels-Alder additions wi
A CONVENIENT SYNTHESIS OF NITRONES BY N-ALKYLATION OF O-TRIMETHYLSILYLOXIMES
LeBel, Norman A.,Balasubramanian, N.
, p. 4331 - 4334 (2007/10/02)
Aldoxime and ketoxime-O-trimethylsilyl ethers can be alkylated with trialkyl-oxonium tetrafluoroborates and alkyl triflates at or below room temperature to produce nitrones in good yields.
SYNTHESIS OF THIOAMIDES FROM ALDONITRONES UTILIZING THIOCARBONYL TRANSFER REAGENTS
Harpp, David N.,MacDonald J. Gavin
, p. 4927 - 4930 (2007/10/02)
The reaction of 1,1'-thiocarbonyldiimidazole and 1,1'-thiocarbonylbis(1,2,4-triazole) with several aldonitrones has been found to afford thioamides in good yield.The effect of solvent polarity and base is discussed.
