The synthesis of phosphaisocoumarins by Cu(I)-catalyzed intramolecular cyclization of o-ethynylphenylphosphonic acid monoesters

被引：95

作者：

Peng, AY ^{[1
]}

Ding, YX ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 49期

关键词：

D O I：

10.1021/ja038627f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cu(I)-catalyzed intramolecular cyclization of o-ethynylphenylphosphonic acid monoethyl esters was examined, and a new class of six-membered phosphorus heterocycles was formed with high regioselectivity and good yields. The present reaction is the first example of intramolecular addition of P?OH to alkynes, which provides a convenient way to synthesize novel phosphorus heterocycles having potential bioactivities. Copyright © 2003 American Chemical Society.

引用

页码：15006 / 15007

页数：2

共 45 条

[31] The first synthesis of 4-trifluoromethyl-2H-pyrans by palladium-catalyzed cyclization of (E)-3-alkynyl-3-trifluoromethyl allylic alcohols
Qing, FL
Gao, WZ
[J]. TETRAHEDRON LETTERS, 2000, 41 (40) : 7727 - 7730
[32] Quin L.D., 2000, GUIDE ORGANOPHOSPHOR
[33] Synthesis of isoquinolines and pyridines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes and unsaturated imines: The total synthesis of decumbenine B
Roesch, KR
Larock, RC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) : 86 - 94
[34] Synthesis of 3-arylisocoumarins, including thunberginols A and B, unsymmetrical 3,4-disubstituted isocoumarins, and 3-ylidenephthalides via iodolactonization of methyl 2-ynylbenzoates or the corresponding carboxylic acids
Rossi, R
Carpita, A
Bellina, F
Stabile, P
Mannina, L
[J]. TETRAHEDRON, 2003, 59 (12) : 2067 - 2081
[35] Palladium-catalyzed intramolecular cyclization of o-ethynylbenzoic acids and o-ethynylbenzamides:: Preparation of isocoumarins and isoquinolin-1-ones
Sashida, H
Kawamukai, A
[J]. SYNTHESIS-STUTTGART, 1999, (07): : 1145 - 1148
[36] Shimoda H, 1998, BIOL PHARM BULL, V21, P809, DOI 10.1248/bpb.21.809
[37] STANG PJ, 1982, SYNTHESIS-STUTTGART, P85
[38] A Ru catalyzed divergence: Oxidative cyclization vs cycloisomerization of bis-homopropargylic alcohols
Trost, BM
Rhee, YH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) : 2528 - 2533
[39] Umehara K, 2000, CHEM PHARM BULL, V48, P566, DOI 10.1248/cpb.48.566
[40] PHOSPHORYLATING AGENTS BY ACTIVATION OF PHOSPHATES WITH ETHOXYACETYLENE
WASSERMAN, HH
COHEN, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (07) : 1817 - &

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