89332-91-2Relevant articles and documents
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
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.
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