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H, C, N NMR, ESI mass spectral and single crystal X-ray structural characterization of three spiro[pyrrolidine-2,3′-oxindoles]
Authors:K Laihia  A Valkonen  E Kolehmainen  A Antonov  D Zhukov  I Fedosov  V Nikiforov
Institution:

aDepartment of Chemistry, P.O. Box 35, FIN-40014, University of Jyväskylä, Finland

bSt. Petersburg State University, Institute of Chemistry, Universitetskii pr., 26, 198504 St. Petersburg, Russia

Abstract:Three spiropyrrolidine-2,3′-oxindoles], 1,1′,2,2′,5′,6′,7′,7′a-octahydro-2-oxo-1′-phenyl-spiro3H-indole-3,3′-3H]-pyrrolizine]-2′-carboxylic acid methyl ester (1), 1,1′,2,2′,5′,6′,7′,7′a-octahydro-2-oxo-1′-nitro-2′-phenyl-spiro3H-indole-3, 3′-3H]-pyrrolizine] (2) and 1,1′,2,2′,5′,6′,7′,7′a-octahydro-2-oxo-1′-nitro-2′-(4″-chlorophenyl)-spiro3H-indole-3,3′-3H]-pyrrolizine] (3) have been synthesized and their 1H, 13C and 15N spectra assigned. The chemical shift assignments are based on Pulsed Field Gradient (PFG) Double Quantum Filter (DQF) 1H, 1H correlation spectroscopy (COSY), PFG 1H, 13C Heteronuclear Multiple Quantum Coherence (HMQC) and PFG 1H,X (X = 13C and 15N) Heteronuclear Multiple Bond Correlation (HMBC) experiments. The single crystal X-ray structures of 13 have been determined. Compounds 1 and 2 crystallized in monoclinic space group C2/c and compound 3 in monoclinic space group P21/c, respectively. Also the ESI-TOF MS data of 13 are given.
Keywords:Spiro[pyrrolidine-2  3′-oxindoles]  1H  13C  15N NMR  Chemical shifts  Single crystal X-ray structure  ESI-TOF mass spectrometry
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