Study of the regioselectivity of vicarious nucleophilic amination of mononitroquinolines with 1,1,1-trimethylhydrazinium iodide (TMHI)

Arkivoc

Volumn 2009, Issue 6, 2009, Pages 84-88

  Grzegozek, Maria ^a   Szpakiewicz, Barbara ^a   Kowalski, Piotr ^a  

^a CRACOW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

1,1,1 trimethylhydrazinium iodide (TMHI); Covalent adducts; Nitroquinolines; PM3 method; Quantum chemical calculations; Vicarious nucleophilic substitution of hydrogen (VNS)

Indexed keywords

EID: 67649553479     PISSN: 1551-7012     EISSN: 15517012     Source Type: Journal    
DOI: 10.3998/ark.5550190.0010.610     Document Type: Article

References (8)

1. Grzegozek, M. J. Heterocycl.Chem. 2008, 45, 1879.
2. Ma̧kosza, M.; Wojciechowski, K. Liebigs Ann/Recueil 1997, 1805.
3. Ma̧kosza, M. Synthesis 1991, 103.
4. Tondys, H.; van der Plas, H.C.; Woźniak, M. J. Heterocycl. Chem. 1985, 22, 353.
5. Woźniak, M.; Barański, A.; Nowak, K. J. Org. Chem. 1987, 52, 5643.
6. Woźniak, M.; Grzegozek, M. Liebigs Ann.Chem. 1993, 823.
7. 1H NMR spectra were recorded on Varian Mercury 300 (300 MHz) spectrometer; the chemical shifts are given in ppm (δ).
8. The PM3 method was used for the semiempirical MO calculations using MOPAC- version 6, molecular orbital package. The starting geometries and intermediary structures were obtained from the corresponding molecular models, fully optimized using keyword PRECISE. The trasition states TS were calculated using SADDLE subroutine. NLLSQ procedure was used for gradient optimization (< 0.1 kcal/mol/Å). The calculations of TS were performed until at least one negative Hessian was obtained. Cartesian coordinates of the transition state TS for mononitroquinolines 1a-e involved in the reaction with TMAI are given in Supplementary Material S1.