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On the discovery and development of tandem 1,4- and 1,2-addition of phosphites to 1-azadienes

Frederik Van Waes (UGent) , Wouter Debrouwer (UGent) , Thomas Heugebaert (UGent) and Christian Stevens (UGent)
(2014) ARKIVOC. p.386-427
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Organization
Abstract
Over the past 15 years we have developed a one-step protocol for the synthesis of 3-phosphonylated aminophosphonates from alpha,beta-unsaturated imines through tandem 1,4-1,2-phosphite addition. This account covers the initial development, mechanistic implications of using different phosphite nucleophiles and the expansion towards oximes, hydrazones and unsaturated imines included in aromatic sextets, e. g. quinolines, phenanthrolines and napthyridines.
Keywords
BETA-UNSATURATED IMINES, MOLECULAR CHARACTERIZATION, BIOLOGICAL-ACTIVITY, ALPHA, ONE-POT SYNTHESIS, SOLVENT-FREE CONDITIONS, diphosphonylation, tandem addition, Phosphonylation, alpha_beta-unsaturated imines, quinolines, alpha_beta-unsaturated hydrazones, alpha_beta-unsaturated oximes, SIGNAL-TRANSDUCTION, 3-COMPONENT SYNTHESIS, phenanthrolines, naphthyridines, KABACHNIK-FIELDS REACTION, ALPHA-AMINO PHOSPHONATES, METABOTROPIC GLUTAMATE-RECEPTOR

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Citation

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MLA
Van Waes, Frederik et al. “On the Discovery and Development of Tandem 1,4- and 1,2-addition of Phosphites to 1-azadienes.” Ed. Viktor Zhdankin. ARKIVOC 1 (2014): 386–427. Print.
APA
Van Waes, F., Debrouwer, W., Heugebaert, T., & Stevens, C. (2014). On the discovery and development of tandem 1,4- and 1,2-addition of phosphites to 1-azadienes. (V. Zhdankin, Ed.)ARKIVOC, (1), 386–427.
Chicago author-date
Van Waes, Frederik, Wouter Debrouwer, Thomas Heugebaert, and Christian Stevens. 2014. “On the Discovery and Development of Tandem 1,4- and 1,2-addition of Phosphites to 1-azadienes.” Ed. Viktor Zhdankin. Arkivoc (1): 386–427.
Chicago author-date (all authors)
Van Waes, Frederik, Wouter Debrouwer, Thomas Heugebaert, and Christian Stevens. 2014. “On the Discovery and Development of Tandem 1,4- and 1,2-addition of Phosphites to 1-azadienes.” Ed. Viktor Zhdankin. Arkivoc (1): 386–427.
Vancouver
1.
Van Waes F, Debrouwer W, Heugebaert T, Stevens C. On the discovery and development of tandem 1,4- and 1,2-addition of phosphites to 1-azadienes. Zhdankin V, editor. ARKIVOC. 2014;(1):386–427.
IEEE
[1]
F. Van Waes, W. Debrouwer, T. Heugebaert, and C. Stevens, “On the discovery and development of tandem 1,4- and 1,2-addition of phosphites to 1-azadienes,” ARKIVOC, no. 1, pp. 386–427, 2014.
@article{5639478,
  abstract     = {Over the past 15 years we have developed a one-step protocol for the synthesis of 3-phosphonylated aminophosphonates from alpha,beta-unsaturated imines through tandem 1,4-1,2-phosphite addition. This account covers the initial development, mechanistic implications of using different phosphite nucleophiles and the expansion towards oximes, hydrazones and unsaturated imines included in aromatic sextets, e. g. quinolines, phenanthrolines and napthyridines.},
  author       = {Van Waes, Frederik and Debrouwer, Wouter and Heugebaert, Thomas and Stevens, Christian},
  editor       = {Zhdankin, Viktor},
  issn         = {1551-7004},
  journal      = {ARKIVOC},
  keywords     = {BETA-UNSATURATED IMINES,MOLECULAR CHARACTERIZATION,BIOLOGICAL-ACTIVITY,ALPHA,ONE-POT SYNTHESIS,SOLVENT-FREE CONDITIONS,diphosphonylation,tandem addition,Phosphonylation,alpha_beta-unsaturated imines,quinolines,alpha_beta-unsaturated hydrazones,alpha_beta-unsaturated oximes,SIGNAL-TRANSDUCTION,3-COMPONENT SYNTHESIS,phenanthrolines,naphthyridines,KABACHNIK-FIELDS REACTION,ALPHA-AMINO PHOSPHONATES,METABOTROPIC GLUTAMATE-RECEPTOR},
  language     = {eng},
  number       = {1},
  pages        = {386--427},
  title        = {On the discovery and development of tandem 1,4- and 1,2-addition of phosphites to 1-azadienes},
  url          = {http://dx.doi.org/10.3998/ark.5550190.p008.648},
  year         = {2014},
}

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