Neighboring-group effect: DBU-promoted ring transformation of substituted isoxazoles to substituted pyrroles

Synthesis

Volumn , Issue 6, 2006, Pages 1021-1027

  Roy, Amrendra K ^a   Pathak, Richa ^a   Yadav, Gaya P ^a   Maulik, Prakas R ^a   Batra, Sanjay ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Baylis Hillman; DBU; Isoxazole; Neighboring group effect; Pyrrole; Ring transformation

Indexed keywords

AROMATIC COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

BAYLIS-HILLMAN; DBU; ISOXAZOLE; NEIGHBORING-GROUP EFFECT; PYRROLE; RING TRANSFORMATION;

NITROGEN COMPOUNDS;

ISOXAZOLE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE;

EID: 33645330693     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926351     Document Type: Article

References (3)

1. CDRI Communication No. 6618.
2. Batra, S.; Roy, A. K. Synthesis 2004, 2550.
3. -1, F(000) = 857.51, rectangular colorless crystal, size = 0.2 × 0.2 × 0.275 mm, 4628 reflections measured [R(int) = 0.05], 3688 unique, wR2 = 0.111 for all data, conventional R = 0.062 [(Δ/σ)max = 000)] on F-values of 1274 reflections with I>2σ(I), S = 0.907 for all data and 247 parameters. Unit cell determination and intensity data collection (2θ = 50°) was performed on a Bruker P4 diffractometer at 293(2) K. Structure solutions by direct methods and refinements by full-matrix least-squares methods on F2. Programs: XSCANS [Siemens Analytical X-ray Instrument Inc.: Madison, Wisconsin, USA 1996], SHELXTL-NT [Bruker AXS Inc.: Madison, Wisconsin, USA 1997]. CCDC (deposit No: 284175) contains the supplementary crystallographic data. These data can be obtained free of charge from www.ccdc.cam.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.