81097-42-9Relevant articles and documents
I2-Mediated oxidative bicyclization of 4-pentenamines to prolinol carbamates with CO2 incorporating oxyamination of the C=C bond
Wang, Sheng,Zhang, Xiaowei,Cao, Chengyao,Chen, Chao,Xi, Chanjuan
supporting information, p. 4515 - 4519 (2017/10/13)
A metal-free oxyamination reaction of alkenes with ambient CO2 is reported. In the presence of I2 and DBU, CO2 is applied in situ as a protecting group to regulate the nucleophilicity of the amino group and facilitate the bicyclization of 4-pentenamines with high chemoselectivity. Moreover, this reaction provided a feasible approach to prepare prolinol carbamates with good tolerance of functional groups and high efficiency under mild conditions.
Pd(0)-catalyzed alkene oxy- and aminoalkynylation with aliphatic bromoacetylenes
Nicolai, Stefano,Sedigh-Zadeh, Raha,Waser, Jeroime
, p. 3783 - 3801 (2013/06/26)
Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins constitute one of the most efficient methods to access them. In this context, oxy- and aminoalkynylation are especially important reactions, because of the numerous transformations possible with the triple bond of acetylenes, yet these methods have been limited to the use of silyl protected acetylenes. Herein, we report the first palladium-catalyzed oxy- and aminoalkynylation using aliphatic bromoalkynes, which proceeded with high diastereoselectivity and functional group tolerance. A one-pot hydrogenation of the triple bond gave then access to alkyl-substituted tetrahydrofurans and pyrroldines. Finally, a detailed study of the side products formed during the reaction gave a first insight into the reaction mechanism.
Safety assessment for the scale-up of an oxime reduction with melted sodium in standard pilot-plant equipment
Breitenmoser, Roland A.,Fink, Thomas,Abele, Stefan
, p. 2008 - 2014 (2013/03/13)
A pilot-plant process is described for the reduction of 2-allyl cyclohexanone oxime with melted sodium in xylenes, toluene, and 4-methyl-2-pentanol. The trans/cis ratio was 3-4:1. Safety data are presented from a range of thermokinetic experiments (heat flow calorimetry, differential scanning calorimetry, and accelerating rate calorimetry). The process has been designed and developed to enable an expedient and safe scale-up in a standard enameled 100-L steel reactor and has been reproduced six times on 209 mol scale (each 4.8 kg sodium). Crystallization of the product 2-allyl cyclohexylamine with oxalic acid from the reaction mixture in tert-butyl methyl ether successfully avoided the yield losses associated with the isolation of the volatile free 2-allyl cyclohexylamine.
The discovery of potent, selective, and orally bioavailable PDE9 inhibitors as potential hypoglycemic agents
DeNinno, Michael P.,Andrews, Melissa,Bell, Andrew S.,Chen, Yue,Eller-Zarbo, Cynthia,Eshelby, Nan,Etienne, John B.,Moore, Dianna E.,Palmer, Michael J.,Visser, Michael S.,Yu, Li J.,Zavadoski, William J.,Michael Gibbs
supporting information; experimental part, p. 2537 - 2541 (2009/12/25)
Starting from a non-selective pyrazolo-pyrimidone lead, the sequential use of parallel medicinal chemistry and directed synthesis led to the discovery of potent, highly selective, and orally bioavailable PDE9 inhibitors. The availability of these tools allowed for a thorough evaluation of the therapeutic potential of PDE9 inhibition.
SYNTHESIS OF MONOCYCLIC ANALOGUES OF A POTENT THROMBOXANE RECEPTOR ANTAGONIST, (+/-)-(5Z)-7-BICYCLOHEPT-2-EXO-YL>HEPTENOIC ACID (S-145)
Kawada, Kenji,Tsushima, Tadahiko
, p. 573 - 578 (2007/10/02)
Several monocyclic analogues of the potent thromboxane-A2 receptor antagonist S-145, i.e. cyclohexane, cyclopentane, tetrahydrofuran, and pyrrolidine, as well as the biclooctane one were synthesized using allylation via oxime dianion and the Barton's method for oxime reduction in the key steps.
Palladium-Catalyzed Cyclization of ω-Olefinic Tosamides. Synthesis of Nonaromatic Nitrogen Heterocycles
Hegedus, Louis S.,McKearin, James M.
, p. 2444 - 2451 (2007/10/02)
The cyclization of aliphatic amino olefins to nonaromatic nitrogen heterocycles nas been accomplished by conversion of the amine to the corresponding p-toluenesulfonamide, followed by Pd(II)-catalyzed intramolecular amination of the olefin.The resulting t
