Format

Send to

Choose Destination
ACS Comb Sci. 2014 Oct 13;16(10):573-7. doi: 10.1021/co500098y. Epub 2014 Sep 12.

Benzhydrylamines via base-mediated intramolecular sp(3) C-arylation of N-benzyl-2-nitrobenzenesulfonamides--advanced intermediates for the synthesis of nitrogenous heterocycles.

Author information

1
Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University , 17. Listopadu 12, 771 46 Olomouc, Czech Republic.

Abstract

N-Benzyl-2-nitrobenzenesulfonamides underwent base-mediated intramolecular arylation at the benzyl sp(3) carbon to yield benzhydrylamines. The presence of electron withdrawing groups on the aromatic ring of the benzyl group was required to facilitate the C-arylation. Unsymmetrically substituted benzhydrylamines are advanced intermediates toward nitrogenous heterocycles, as exemplified in the syntheses of indazole oxides and quinazolines.

KEYWORDS:

C−C bond formation; arylation; benzhydrylamine; heterocycle; indazole oxide; nitrobenzenesulfonamides; quinazoline

PMID:
25180543
DOI:
10.1021/co500098y
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center