Bulletin of the Chemical Society of Japan p. 2542 - 1549 (1994)
Update date:2022-08-02
Topics:
Kodera
Watanabe
Imada
Murahashi
N,N-Disubstituted and cyclic hydroxylamines can be converted into the corresponding imines efficiently upon treatment with anhydrons titanium trichloride in THF at room temperature. Similar treatment of N-allylhydroxylamines with anhydrous titanium trichloride gives 1-azadienes, which are versatile synthetie intermediates for aza-Diels-Alder reactions. On the other hand, the same hydroxylamines can be converted into the corresponding secondary amines upon treatment with aqueous titanium trichloride in methanol. It is noteworthy that optically active hydroxylamines, which have chirality at the α-position to nitrogen, can be converted into optically active secondary amines without loss of chirality. Dihydro-2(1H)-quinolinones can be prepared upon treatment of 1-hydroxy-3,4-dihydro-2(1H)-quinolinones with aqueous titanium trichloride. The substrates of N,N-disubstituted and cyclic hydroxylamines can be prepared readily upon treatment of nitrones with nucleophiles. Since nitrones can be prepared by metal-catalyzed oxidations of secondary amines with hydrogen peroxide, the present titanium(III)-promoted reaction of hydroxylamines will provide a convenient method for the synthesis of either α-substituted imines or amines from secondary amines.
View MoreABA Chemicals (Shanghai) Limited
Contact:021- 5115 9199-232
Address:Suite 18D, #201 Ningxia Road,
Hangzhou Hysen Pharma co.,Ltd.
website:http://www.hysenpharma.cn/
Contact:0086-571-88298791
Address:#701,Gudun Road Hangzhou
Contact:+86--29-82745382
Address:Development Area Of Lantian Country,Xi'an Shanxi.China
Shanghai Forever Biotech Co., Ltd.
Contact:+86-21-69734790
Address:Room 5017/5019、5022、5024 of Technology Innovation Centre, No.1155, Gongyuan East Rd, QingPu District, Shanghai China.
Suzhou Lixin Pharmaceutical Co., Ltd.
Contact:86-512-88169812
Address:21 Tangxi Road, Suzhou New District, Suzhou 215151
Doi:10.1021/jf011129a
(2002)Doi:10.1002/1521-4184(200212)335:9<411::AID-ARDP411>3.0.CO;2-D
(2002)Doi:10.1016/j.tetlet.2004.06.064
(2004)Doi:10.1248/cpb.32.4545
(1984)Doi:10.1016/S0040-4039(98)01790-0
(1998)Doi:10.1007/BF00958816
(1980)