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- Title
Study of the regioselectivity of vicarious nucleophilic amination of mononitroquinolines with 1,1,1-trimethylhydrazinium iodide (TMHI).
- Authors
Grzegożek, Maria; Szpakiewicz, Barbara; Kowalski, Piotr
- Abstract
The intermediary, covalent s adducts formed in the reaction of nitroquinolines with the ylide generated from 1,1,1-trimethylhydrazinium iodide (TMHI) were detected by 1H NMR spectroscopy. Quantum-chemical calculations of the transition state (TS) energy and heats of formation of the σ adducts were done. The results of the calculations agree with high regioselectivity observed for the amination of 3-, 5-, 6-, 7- and 8-nitroquinolines with (TMHI) via a vicarious nucleophilic substitution (VNS) reaction. High yields of the products substituted with amino substituent, mainly in the ortho position relation to the nitro group, are obtained.
- Subjects
ADDUCTION; NITROQUINOLINE oxide; YLIDES; TRIMETHYL ammonium compounds; IODIDES; SPECTRUM analysis; NUCLEOPHILIC reactions; AMINATION; NITRO compounds
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2009, p84
- ISSN
1551-7004
- Publication type
Article