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[4+2] Cycloadditions of 1-phosphono-1,3-butadienes with nitroso heterodienophiles: a versatile synthetic route for polyfunctionalized aminophosphonic derivatives

(2010) JOURNAL OF ORGANIC CHEMISTRY. 75(16). p.5478-5486
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Abstract
The hetero-Diels-Alder (HDA) reaction of 1-(diethoxyphosphonyl)-1,3-butadiene, 1-(dibenzyloxyphosphonyl)-1,3-butadiene, and 1-(diethoxyphosphonyl)-3-tert-butyldimethylsilyloxy-1,3-butadiene with various nitroso heterodienophiles has been investigated as a new synthetic route for aminophosphonic derivatives. The HDA cycloadditions regioselectively led to the proximal isomers, i.e., presenting the NR3 group in the meta position regarding the phosphonate substituent. From the resulting 6-phosphono-3,6-dihydro-1,2-oxazine cycloadducts, a limited number of chemical steps were allowed to obtain a significant variety of aminophosphonic compounds of potential interest in medicinal chemistry. This has been illustrated through the synthesis of (Z)-4-(o-tolylamino)-1-hydroxybut-2-enylphosphonic acid, diethyl 3,4-dihydroxy-1-o-tolylpyrrolidin-2-yl-2-phosphonate, 4-(o-tolylamino)-1,2,3-trihydroxybutylphosphonic acid, diethyl 3-(2-(o-tolylamino)-1-hydroxyethyl)oxiran-2-yl-2-phosphonate, and diethyl 4,5-dihydroxymorpholin-6-yl-6-phosphonate.
Keywords
DIENOPHILES, ACIDS, CHEMISTRY, ALDEHYDES, PHOSPHONATES, CARBOCYCLIC NUCLEOSIDES, NITROSOCARBONYL COMPOUNDS, DIELS-ALDER REACTIONS, PRACTICAL SYNTHESIS, SILYL ENOL ETHERS

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Citation

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MLA
Monbaliu, Jean-Christophe, Bernard Tinant, and Jacqueline Marchand-Brynaert. “[4+2] Cycloadditions of 1-phosphono-1,3-butadienes with Nitroso Heterodienophiles: a Versatile Synthetic Route for Polyfunctionalized Aminophosphonic Derivatives.” JOURNAL OF ORGANIC CHEMISTRY 75.16 (2010): 5478–5486. Print.
APA
Monbaliu, J.-C., Tinant, B., & Marchand-Brynaert, J. (2010). [4+2] Cycloadditions of 1-phosphono-1,3-butadienes with nitroso heterodienophiles: a versatile synthetic route for polyfunctionalized aminophosphonic derivatives. JOURNAL OF ORGANIC CHEMISTRY, 75(16), 5478–5486.
Chicago author-date
Monbaliu, Jean-Christophe, Bernard Tinant, and Jacqueline Marchand-Brynaert. 2010. “[4+2] Cycloadditions of 1-phosphono-1,3-butadienes with Nitroso Heterodienophiles: a Versatile Synthetic Route for Polyfunctionalized Aminophosphonic Derivatives.” Journal of Organic Chemistry 75 (16): 5478–5486.
Chicago author-date (all authors)
Monbaliu, Jean-Christophe, Bernard Tinant, and Jacqueline Marchand-Brynaert. 2010. “[4+2] Cycloadditions of 1-phosphono-1,3-butadienes with Nitroso Heterodienophiles: a Versatile Synthetic Route for Polyfunctionalized Aminophosphonic Derivatives.” Journal of Organic Chemistry 75 (16): 5478–5486.
Vancouver
1.
Monbaliu J-C, Tinant B, Marchand-Brynaert J. [4+2] Cycloadditions of 1-phosphono-1,3-butadienes with nitroso heterodienophiles: a versatile synthetic route for polyfunctionalized aminophosphonic derivatives. JOURNAL OF ORGANIC CHEMISTRY. 2010;75(16):5478–86.
IEEE
[1]
J.-C. Monbaliu, B. Tinant, and J. Marchand-Brynaert, “[4+2] Cycloadditions of 1-phosphono-1,3-butadienes with nitroso heterodienophiles: a versatile synthetic route for polyfunctionalized aminophosphonic derivatives,” JOURNAL OF ORGANIC CHEMISTRY, vol. 75, no. 16, pp. 5478–5486, 2010.
@article{852423,
  abstract     = {The hetero-Diels-Alder (HDA) reaction of 1-(diethoxyphosphonyl)-1,3-butadiene, 1-(dibenzyloxyphosphonyl)-1,3-butadiene, and 1-(diethoxyphosphonyl)-3-tert-butyldimethylsilyloxy-1,3-butadiene with various nitroso heterodienophiles has been investigated as a new synthetic route for aminophosphonic derivatives. The HDA cycloadditions regioselectively led to the proximal isomers, i.e., presenting the NR3 group in the meta position regarding the phosphonate substituent. From the resulting 6-phosphono-3,6-dihydro-1,2-oxazine cycloadducts, a limited number of chemical steps were allowed to obtain a significant variety of aminophosphonic compounds of potential interest in medicinal chemistry. This has been illustrated through the synthesis of (Z)-4-(o-tolylamino)-1-hydroxybut-2-enylphosphonic acid, diethyl 3,4-dihydroxy-1-o-tolylpyrrolidin-2-yl-2-phosphonate, 4-(o-tolylamino)-1,2,3-trihydroxybutylphosphonic acid, diethyl 3-(2-(o-tolylamino)-1-hydroxyethyl)oxiran-2-yl-2-phosphonate, and diethyl 4,5-dihydroxymorpholin-6-yl-6-phosphonate.},
  author       = {Monbaliu, Jean-Christophe and Tinant, Bernard and Marchand-Brynaert, Jacqueline},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {DIENOPHILES,ACIDS,CHEMISTRY,ALDEHYDES,PHOSPHONATES,CARBOCYCLIC NUCLEOSIDES,NITROSOCARBONYL COMPOUNDS,DIELS-ALDER REACTIONS,PRACTICAL SYNTHESIS,SILYL ENOL ETHERS},
  language     = {eng},
  number       = {16},
  pages        = {5478--5486},
  title        = {[4+2] Cycloadditions of 1-phosphono-1,3-butadienes with nitroso heterodienophiles: a versatile synthetic route for polyfunctionalized aminophosphonic derivatives},
  url          = {http://dx.doi.org/10.1021/jo100230r},
  volume       = {75},
  year         = {2010},
}

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