Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2007(2): 231-234
DOI: 10.1055/s-2006-958951
DOI: 10.1055/s-2006-958951
PAPER
© Georg Thieme Verlag Stuttgart · New York
Application of 2,2,2-Trichloroethoxycarbonyl Protection to Aminoacridines
Further Information
Received
11 September 2006
Publication Date:
21 December 2006 (online)
Publication History
Publication Date:
21 December 2006 (online)
![](https://www.thieme-connect.de/media/synthesis/200702/lookinside/thumbnails/10.1055-s-2006-958951-1.jpg)
Abstract
The 2,2,2-trichloroethoxycarbonyl (Troc) group has been successfully used as a protecting group for aminoacridines. Unlike aliphatic amines, deprotection of these aromatic amines yields significant amounts (12-29%) of stable 2,2-dichloroethoxycarbonyl (Dioc) by-products. Formation of bis-carbamates, through the introduction of butoxycarbonyl (Boc) moieties as temporary protecting groups, efficiently solves this problem.
Key words
fused-ring systems - heterocycles - amino protecting group - carbamate
- 1
Charmantray F.Demeunynck M.Carrez D.Croisy A.Lansiaux A.Bailly C.Colson P. J. Med. Chem. 2003, 46: 967 - 2
Hancock G.Galpin IJ.Morgan BA. Tetrahedron Lett. 1982, 23: 249 - 3
Dong Q.Anderson CE.Ciufolini MA. Tetrahedron Lett. 1995, 36: 5681 - 4
Somsak L.Czifrak K.Veres E. Tetrahedron Lett. 2004, 45: 9095 - 5
Doi T.Numajiri Y.Munakata A.Takahashi T. Org. Lett. 2006, 8: 531 - 6
Valluri M.Mineno T.Hindapur RM.Avery MA. Tetrahedron Lett. 2001, 42: 7153 - 7
Tokimoto H.Fukase K. Tetrahedron Lett. 2005, 46: 6831 - 8
Zhu X.Schmidt RR. Synthesis 2003, 1262 - 9
Ando H.Koike Y.Ishida H.Kiso M. Tetrahedron Lett. 2003, 44: 6883 - 10
Xue J.Khaja SD.Locke RD.Matta KL. Synlett 2004, 861 - 11
Overman LE.Freerks RL. J. Org. Chem. 1981, 46: 2833 -
12a
Greene TW.Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: John Wiley and Sons; London: 1999. -
12b
Kociensky PJ. Protecting Groups 3rd ed.: Georg Thieme Verlag; Stuttgart: 2005. - 13
Woodward RB.Heusler K.Gosteli J.Naegeli P.Oppolzer W.Ramage R.Ranganathan S.Vorbrüggen H. J. Am. Chem. Soc. 1966, 88: 852 - 14
Mineno T.Choi S.-R.Avery MA. Synlett 2002, 883 - 15
Semmelhack MF.Heinsohn GE. J. Am. Chem. Soc. 1972, 94: 5139