180475-48-3Relevant articles and documents
Intramolecular azide-alkene 1,3-dipolar cycloaddition/enamine addition(s) cascade reaction: Synthesis of nitrogen-containing heterocycles
De Miguel, Irene,Herradon, Bernardo,Mann, Enrique
supporting information; experimental part, p. 1731 - 1736 (2012/07/28)
A cascade intramolecular azide-alkene 1,3-dipolar cycloaddition/1,2 enamine and/or 1,4 enamine addition reaction sequence has been developed, and provides access to a variety of nitrogen containing heterocycles from readily available ω-azido alkenes. Copy
Formaldehyde dialkylhydrazones as neutral formyl anion and cyanide equivalents: Nucleophilic addition to conjugated enones
Diez,Fernandez,Gasch,Lassaletta,Llera,Martin-Zamora,Vazquez
, p. 5144 - 5155 (2007/10/03)
A versatile methodology for the nucleophihc formylation and cyanation of conjugated enones is reported. The procedure is based on the use of formaldehyde dimethylhydrazone, which, acting as a neutral formyl anion equivalent, adds to preformed trialkylsilyl-enone complexes. Both 4-(silyl- oxy)-3-enal hydrazones 3 or deprotected 4-oxo aldehyde monohydrazones 4 can be obtained at products depending on quenching conditions. In full analogy, an asymmetric version of the reaction using chiral formaldehyde SAMP- hydrazone as a neutral synthon of the chiral formyl anion has been developed, giving rise to the corresponding adducts 5 and 6 in good yields and with excellent diastereoselectivities (de 85-≤98%). Ozonolysis or HCl-mediated hydrolysis of adducts 4 and 6 readily affords racemic and optically enriched 4-oxo aldehydes 7, respectively. Additionally, high-yielding MMPP-oxidative cleavage of 4-oxo hydrazones 4 and 6 has been performed to obtain 4-oxo nitriles 8 in racemic and optically enriched forms, respectively. In this way, interesting chiral bifunctional building blocks, some of them bearing newly created stereogenic quaternary centers, have been efficiently synthesized.
REACTION OF METHYL-SUBSTITUTED 7-CHLORO- AND 7,7-DICHLOROBICYCLOheptan-2-ones WITH SODIUM METHOXIDE AND THIOPHENOLATE
Kulinkovich, O. G.,Tishchenko, I. G.,Romashin, Yu. N.
, p. 81 - 85 (2007/10/02)
The reaction of exo-7-chloro-6-methylbicycloheptan-2-one, exo-7-chloro-4,4,6-trimethylbicycloheptan-2-one, 7,7-dichloro-6-methylbicyclo-heptan-2-one, and 7,7-dichloro-4,4,6-trimethylbicycloheptan-2-one with sodium methoxide takes place with opening of the cyclopropane ring and the formation of the corresponding 3-dimethoxymethyl- and 3-trimethoxymethylcyclohexanones.The reaction with sodium thiophenolate leads to the product from substitution of the exo-chlorine atom by the phenylthio group with retention of the three-membered ring.
