72228-95-6Relevant academic research and scientific papers
Intermolecular metal-free cyclopropanation of alkenes using tosylhydrazones
Barluenga, Jose,Quinones, Noelia,Tomas-Gamasa, Maria,Cabal, Maria-Paz
supporting information; experimental part, p. 2312 - 2317 (2012/06/01)
We describe the first general method for the metal-free cyclopropanation of alkenes by using N-tosylhydrazones as an in situ source of diazo compounds. This new method works with a wide variety of alkenes (styrene derivatives, dienes, enynes, and electron-deficient alkenes) by using N-tosylhydrazones derived from various ketones or aldehydes (aromatic, aliphatic, enones). The reaction is performed with the use of K2CO3 as a base to form the diazo species and is compatible with a wide array of functional groups. A new procedure for the synthesis of cyclopropanes by the formal cyclopropanation of carbonyl compounds and alkenes is described. This metal-free reaction proceeds through the base-promoted decomposition of tosylhydrazones. There is significant tolerance of the functional groups, enabling cyclopropanation in the presence of functionalities often not compatible with other methodologies.
N,N-dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists
Arvidsson,Johansson,Hacksell,Nilsson,Svensson,Hjorth,Magnusson,Carlsson,Lindberg,Andersson,Sanchez,Wikstrom,Sundell
, p. 92 - 99 (2007/10/02)
N,N-Dialkylated monophenolic derivatives of trans-2-phenylcyclopropylamine were synthesized and tested for central 5-hydroxytryptamine (5-HT) and dopamine (DA) receptor stimulating activity by use of a biochemical test method in rats. A hydroxy substituent in the 2- or 3-position of the phenyl ring was required for 5-HT-receptor stimulation. N,N-Diethyl or N,N-di-n-propyl substitution gave the most potent 5-HT-receptor agonists. The 4-hydroxy and 3,4-dihydroxy derivatives of trans-2-phenyl-N,N-di-n-propylcyclopropylamine were inactive at central DA and 5-HT receptors. In contrast, the corresponding 3-hydroxy derivative 18 and some of its derivatives weakly affected both DA and NE synthesis. Two of the most potent 5-HT-receptor agonists, trans-2-(2-hydroxyphenyl)-N,N-di-n-propylcyclopropylamine (8) and the 3-hydroxy isomer 18 were resolved into the enantiomers. The 1R,2S enantiomers of 8 and 18 displayed 5-HT activity, while the 1S,2R enantiomers were inactive. Compound (1R,2S)-18, but not (1R,2S)-8, weakly affected rat brain DA and NE synthesis.
Transition-Metal-Catalyzed Reactions of Diazo Compounds. 1. Cyclopropanation of Double Bonds
Anciaux, Andre J.,Hubert, Andre J.,Noels, Alfred F.,Petiniot, N.,Teyssie, Philippe
, p. 695 - 702 (2007/10/02)
Rhodium(II) and palladium(II) carboxylates are efficient catalysts for the cyclopropanation of olefins by diazo esters.Intramolecular competitions within diolefins and intermolecular competitions between pairs of monoolefins showed quite different cyclopr
