162338-03-6Relevant articles and documents
Highly chemoselective aerobic oxidation of amino alcohols into amino carbonyl compounds
Sasano, Yusuke,Nagasawa, Shota,Yamazaki, Mai,Shibuya, Masatoshi,Park, Jaiwook,Iwabuchi, Yoshiharu
supporting information, p. 3236 - 3240 (2014/04/03)
The direct oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has often posed serious challenges in organic synthesis and has constrained chemists to adopting an indirect route, such as a protection/deprotection strategy, to attain their goal. Described herein is a highly chemoselective aerobic oxidation of unprotected amino alcohols to their amino carbonyl compounds in which 2-azaadamantane N-oxyl (AZADO)/copper catalysis is used. The catalytic system developed leads to the alcohol-selective oxidation of various unprotected amino alcohols, carrying a primary, secondary, or tertiary amino group, in good to high yield at ambient temperature with exposure to air, thus offering flexibility in the synthesis of nitrogen-containing compounds. Strong as an ox: The highly chemoselective aerobic oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has been achieved by using 2-azaadamantane N-oxyl (AZADO)/copper catalysis. This catalytic system oxidizes not only alcohols with tertiary amino groups but also those with secondary and primary amines in good to high yield at ambient temperature in air. bpy=2,2-bipyridyl, DMAP=4-(N,N-dimethylamino)pyridine.
A rapid and practical entry into cis-1,4-aminocyclohexanols
Gallou, Fabrice,Han, Bo,Lu, Jiang,Seeger-Weibel, Manuela,Stoessel, Anne-Florence,Allmendinger, Simon
experimental part, p. 1419 - 1422 (2010/05/03)
A selective and practical approach for the formation of cis-1,4-aminocyclohexanol was developed. The key transformation involves a one-pot imine formation/ Lewis acid-directed imine reduction and results in a highly selective attack of the reducing agent. This simple and practical method is easily amenable to large-scale synthesis.
A simple and efficient synthesis of N-substituted cyclohex-3-enamines
Alvarez-Perez, Monica,Marco-Contelles, Jose
experimental part, p. 3649 - 3653 (2010/04/05)
A straightforward preparation of N-substituted cyclohex-3-enamines starting from the commercially available trans-4-aminocyclohexanol hydrochloride is described. Cyclohex-3-enamino-functionalized compounds have proven to be interesting intermediates in me
2(1H)-Quinolinone derivatives as novel anti-arteriostenotic agents showing anti-thrombotic and anti-hyperplastic activities
Koga, Yasuo,Kihara, Yoshito,Okada, Minoru,Inoue, Yoshihiro,Tochizawa, Shirou,Toga, Kazuyuki,Tachibana, Kazue,Kimura, Yukio,Nishi, Takao,Hidaka, Hiroyoshi
, p. 1471 - 1476 (2007/10/03)
In order to search for anti-arteriostenotic agents, a series of 2(1H)- quinolinone derivatives was synthesized and evaluated for anti-thrombotic activity and for anti-hyperplastic activity. From this series, (-)-6-[3-[3- cyclopropyl-3-[(1R,2R)-2-hydroxycycyclohexyl]ureido]propoxy]-2(1H)- quinolinone (1p, OPC-33509) was selected as the best candidate by balancing the efficacy on anti-thrombosis and anti-hyperplasia.
A simple method of preparation of 7-alkyl-7-azabicyclo[2.2.1] heptanes
Hassner, Alfred,Belostotskii, Anatoly M.
, p. 1709 - 1712 (2007/10/02)
Action of triphenylphosphine - carbon tetrachloride on the trans-4-alkylaminocyclohexanols leads to 7-alkyl-7-azabicyclo[2.2.1]heptanes in the good yields. The starting aminoalcohols are easily available from the monoethylene ketal of 1,4-cyclohexanedione and primary amines in a four step process without isolation of intermediates.
