Title
Synthesis and characterization of 4'-amino and 4'-nitro derivatives of 4-N, N-dimethylaminotriphenylmethane as precursors for a proximate malachite green metabolite
Document Type
Article
Date of Original Version
9-15-2000
Abstract
This paper describes the preparation of 4'-amino (2) and 4'-nitro (3) derivatives of 4-N, N-dimethylaminotriphenylmethane as precursors for presumed DNA-binding metabolites of malachite green. The primary amine 2 was synthesized via a condensation of 4-lithiated bis-(N, N-trimethylsilyl)aniline and 4-(dimethylamino)benzophenone. A simple nitro-dediazoniation reaction of 2 failed to afford 3, but gave exclusively a mixture derived from hydro-dediazoniation followed by nitration and N-dealkylative-N-nitrosation. Direct nitration of N, N-dimethylaminotriphenylmethane, however, afforded 3 as well as other nitro isomers.
Publication Title, e.g., Journal
Tetrahedron
Volume
56
Issue
38
Citation/Publisher Attribution
Cho, Bongsup P., Lonnie R. Blankenship, Joanna D. Moody, Daniel R. Doerge, Frederick A. Beland, and Sandra J. Culp. "Synthesis and characterization of 4'-amino and 4'-nitro derivatives of 4-N, N-dimethylaminotriphenylmethane as precursors for a proximate malachite green metabolite." Tetrahedron 56, 38 (2000): 7379-7388. doi: 10.1016/S0040-4020(00)00649-9.