An efficient synthesis of [N-15]-carbazole from [N-15]-aniline

Authors
Peterson, MA Nilsson, BL
Citation
Ma. Peterson et Bl. Nilsson, An efficient synthesis of [N-15]-carbazole from [N-15]-aniline, SYN COMMUN, 29(21), 1999, pp. 3821-3827
Citations number
10
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
21
Year of publication
1999
Pages
3821 - 3827
Database
ISI
SICI code
0039-7911(1999)29:21<3821:AESO[F>2.0.ZU;2-R
Abstract
A reaction sequence involving ortho-lithiation of [N-15]-(tert-Butoxycarbon yl)aniline, quenching with Bu3SnCl, palladium catalyzed coupling with bromo benzene, and deprotection provides efficient access to [N-15]-2-aminobiphen yl (4). Compound 4 is converted to [N-15]-carbazole via diazotization, trea tment with NaN3, and heating to promote intramolecular nitrene insertion.