Beilstein Journal of Organic Chemistry p. 832 - 837 (2013)
Update date:2022-08-05
Topics:
Pereira, Vera Lucia Patrocinio
Da Silva Moura, Andre Luiz
Vieira, Daniel Pais Pires
De Carvalho, Leandro Lara
Torres, Eliz Regina Bueno
Da Silva Costa, Jeronimo
New chiral (S,E)-γ-N,N-dibenzylated nitroalkenes 2a-c were synthesized from natural L-(α)-amino acids in five steps with overall yields of 68-88%. The conjugate addition of hydride, methoxide, nitronate and azide nucleophiles to 2a-c led to the corresponding chiral 1,3-nitroamines in 74-90% yield. The conjugate addition of cyanide anion to 2a,b was followed by HNO2 elimination affording chiral aminated acrylonitriles (73-98%). On the other hand, the azide anion reacted with 2a, in acetonitrile, via a [3 + 2]-cycloaddition in which HNO2 was lost, providing the corresponding 1,2,3-triazole derivative. Direct reduction of 1,3- nitroamine derivatives 9a,b produced the corresponding 1,3-diamines in good yields.
View MoreShanghai Pinewood Fine Chemical Co., Ltd.
website:http://www.pinewoodchem.com
Contact:0086-21-62417129,62414096
Address:Suite B, 27F, No.2, Lane 600, Tianshan Road, Shanghai
KAIYUAN CHEMICAL COMPANY LIMITED.
website:http://www.kaiyuanchem.com
Contact:+86-22-59891255/66/77
Address:B-2205, Kuangshi International Building, Yingbin Road, XiangLuo Bay Business District, Binhai New area, Tianjin, China.
Contact:+86-519-86339586,13584329896
Address:Changzhou Scientific and Education Park
Henan PURUI Pharmaceutical Co., Ltd.
website:http://www.puruipharm.com
Contact:17739583555
Address:Yezhuangqiao,Xihua town, Henan province
NINGBO YINLIANG FOREIGN TRADE CO., LTD.
Contact:+86-574-87834016 / 87898057
Address:23F NO.666JINYU ROAD,YINGZHOU DISTRICT,NINGBO.CHINA
Doi:10.1055/s-1987-28025
(1987)Doi:10.1135/cccc19921553
(1992)Doi:10.1016/j.bmc.2008.06.037
(2008)Doi:10.1134/S1070363213050253
()Doi:10.1039/c5ra17827d
(2015)Doi:10.1246/bcsj.65.2259
(1992)