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References (25)
-
Wei Tang, Yixiang Ding, Yixiang Ding (2008)
Pd(II)-catalyzed coupling–cyclization reaction of o-ethylnylphenylphosphonamides monoesters with allyl halideTetrahedron, 64
-
A. Peng, Yixiang Ding (2003)
The synthesis of phosphaisocoumarins by Cu(I)-catalyzed intramolecular cyclization of o-ethynylphenylphosphonic acid monoesters.Journal of the American Chemical Society, 125 49
-
Maud Jacubert, Abdallah Hamze, O. Provot, J. Peyrat, J. Brion, M. Alami (2009)
p-Toluenesulfonic acid-mediated cyclization of o-(1-alkynyl)anisoles or thioanisoles: synthesis of 2-arylsubstituted benzofurans and benzothiophenesTetrahedron Letters, 50
-
M. Heravi, S. Sadjadi (2009)
Recent Advances in the Application of the Sonogashira Method in the Synthesis of Heterocyclic CompoundsChemInform, 40
-
Yoshinori Yamamoto, I. Gridnev, N. Patil, T. Jin (2009)
Alkyne activation with Brønsted acids, iodine, or gold complexes, and its fate leading to synthetic application.Chemical communications, 34
-
J. Sangshetti, N. Kokare, S. Kotharkar, D. Shinde (2008)
Sodium Bisulfite as an Efficient and Inexpensive Catalyst for the One-pot Synthesis of 2,4,5-Triaryl-1H-imidazoles from Benzil or Benzoin and Aromatic AldehydesMonatshefte für Chemie - Chemical Monthly, 139
-
Liang Xie, Jing Ma, Yixiang Ding (2008)
Synthesis of 3‐Allyl‐4‐phosphachromones by Cyclized Coupling of Ethyl o‐Hydroxyphenyl(ethynyl)phosphinate with Allyl BromideChinese Journal of Chemistry, 26
-
Liang Xie, Jing Ma, Yixiang Ding (2008)
Ag(I)-catalyzed cyclization reaction of ethyl o-hydroxyphenylethynylphosphinates to phosphachromonesTetrahedron Letters, 49
-
C. Brennan, C. Johnson, P. Mcdonnell (1989)
Ring closure to ynone systems: 5- and 6-endo- and -exo-dig modesJournal of The Chemical Society-perkin Transactions 1
-
Malik Hellal, J. Bourguignon, F. Bihel (2007)
6-Endo-dig cyclization of heteroarylesters to alkynes promoted by Lewis acid catalyst in the presence of Bronsted acidTetrahedron Letters, 49
-
A. Peng, Yixiang Ding (2004)
Synthesis of phosphaisocoumarins via iodocyclization.Organic letters, 6 7
-
A. Peng, Yixiang Ding (2005)
Synthesis of 4-halophosphaisocoumarins via halocyclization of 2-(1-alkynyl)phenylphosphonatesTetrahedron, 61
-
A. Bhat, J. Whetstone, R. Brueggemeier (1999)
Novel synthetic routes suitable for constructing benzopyrone combinatorial librariesTetrahedron Letters, 40
-
M. Uchiyama, Hiroki Ozawa, Kazuya Takuma, Yotaro Matsumoto, M. Yonehara, K. Hiroya, T. Sakamoto* (2006)
Regiocontrolled intramolecular cyclizations of carboxylic acids to carbon-carbon triple bonds promoted by acid or base catalyst.Organic letters, 8 24
-
Maud Jacubert, O. Provot, J. Peyrat, Abdallah Hamze, J. Brion, M. Alami (2010)
p-Toluenesulfonic acid-promoted selective functionalization of unsymmetrical arylalkynes: a regioselective access to various arylketones and heterocyclesTetrahedron, 66
-
Fan-hong Wu, Xueyan Yang, Zhonghua Wang, Wei‐yuan Huang (2007)
Studies on sulfinatodehalogenation: The addition of polyfluoroalkyl iodides to olefins promoted by sodium bisulfite and sodium sulfiteJournal of Fluorine Chemistry, 128
-
L. Mcgarry, M. Detty (1990)
Synthesis of highly functionalized flavones and chromones using cycloacylation reactions and C-3 functionalization. A total synthesis of hormothamnioneJournal of Organic Chemistry, 55
-
J. Baldwin, J. Cutting, W. Dupont, L. Kruse, Lee Silberman, Richard Thomas (1976)
5-Endo-trigonal reactions: a disfavoured ring closureJournal of The Chemical Society, Chemical Communications
-
Wei Tang, Yixiang Ding (2006)
Synthesis of phosphaisoquinolin-1-ones by Pd(II)-catalyzed cyclization of o-(1-alkynyl)phenylphosphonamide monoesters.The Journal of organic chemistry, 71 22
-
C. Kanazawa, M. Terada (2007)
Organic-base-catalyzed synthesis of phthalides via highly regioselective intramolecular cyclization reactionTetrahedron Letters, 48
-
M. Álvaro, H. García, S. Iborra, M. Miranda, J. Primo (1987)
New photochemical approaches to the synthesis of chromonesTetrahedron, 43
-
Zheng-Zheng Huang, S. Ye, W. Xia, Yong Tang (2001)
A practical catalytic Wittig-type reactionChemical Communications
-
A. Peng, Feiyue Hao, Baojian Li, Zheng Wang, Yidan Du (2008)
An efficient route to 4-halophosphaisocoumarins via CuX2-mediated direct halocyclization of 2-(1-alkynyl)phenylphosphonic acid diesters.The Journal of organic chemistry, 73 22
-
A. Peng, Yixiang Ding (2005)
Synthesis of 2H-1,2-oxaphosphorin 2-oxides via Ag2CO3-catalyzed cyclization of (Z)-2-alken-4-ynylphosphonic monoesters.Organic letters, 7 15
-
Xiangming Han, Huiqiang Ma, Yu-lu Wang (2008)
A simple and efficient synthesis of 2-aryl-substituted benzimidazolesRussian Journal of Organic Chemistry, 44
- Publisher
- Wiley
- Copyright
- Copyright © 2011 Wiley Periodicals, Inc.
- ISSN
- 1042-7163
- eISSN
- 1098-1071
- DOI
- 10.1002/hc.20728
- Publisher site
- See Article on Publisher Site
Abstract
In this work, we found that acids (i.e., HCl and NaHSO3) rather than bases could catalyze the cyclization of o‐alkynylphenylphosphonic acid monoesters at slow rates and give phosphaisocoumarins in low to medium yields, whereas the cyclization of (o‐hydroxyphenyl)ethynylphosphinates proceeded very smoothly under basic conditions rather than acidic conditions, and a series of phosphachromones could be prepared in excellent yields at room temperature using K2CO3 as catalyst. This is the first example of the synthesis of phosphorus heterocycles via acid/base‐catalyzed intramolecular cyclization of alkynes. Possible mechanisms were discussed. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:649–652, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20728
Journal
Heteroatom Chemistry – Wiley
Published: Sep 1, 2011