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

Jean-Christophe Monbaliu UGent, Bernard Tinant and Jacqueline Marchand-Brynaert (2010) JOURNAL OF ORGANIC CHEMISTRY. 75(16). p.5478-5486
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
DIENOPHILES, ACIDS, CHEMISTRY, ALDEHYDES, PHOSPHONATES, CARBOCYCLIC NUCLEOSIDES, NITROSOCARBONYL COMPOUNDS, DIELS-ALDER REACTIONS, PRACTICAL SYNTHESIS, SILYL ENOL ETHERS
journal title
JOURNAL OF ORGANIC CHEMISTRY
J. Org. Chem
volume
75
issue
16
pages
5478 - 5486
Web of Science type
Article
Web of Science id
000280798900006
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
4.002 (2010)
JCR rank
8/56 (2010)
JCR quartile
1 (2010)
ISSN
0022-3263
DOI
10.1021/jo100230r
language
English
UGent publication?
no
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
852423
handle
http://hdl.handle.net/1854/LU-852423
date created
2010-02-05 09:33:49
date last changed
2012-01-24 12:48:11
@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},
  keyword      = {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},
}

Chicago
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.
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.
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.
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.