CuI-Catalyzed [3+2] Cycloaddition of Hindered Vinylidenebisphosphonates (VBP) with Azomethine Imines for Highly Regioselective Access to Dinitrogen-Heterobicycle-Containing Bisphosphonates

被引：1

作者：

Zhu, Zhongxiang ^{[1
]}

Wang, Qinghe ^{[1
]}

Kong, Dulin ^{[2
]}

Huang, Tiao ^{[1
]}

Wu, Mingshu ^{[1
]}

机构：

[1] Hainan Normal Univ, Coll Chem & Chem Engn, Key Lab Trop Med Plant Chem, Minist Educ, Haikou 571158, Hainan, Peoples R China

[2] Hainan Med Univ, Sch Pharmaceut Sci, Haikou 571199, Hainan, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 13期

关键词：

copper(I) catalysis; azomethine imines; 1,3-dipolar cycloaddition; vinylidenebisphosphonate; dinitrogen-fused heterocycles; bisphosphonates; 1,3-DIPOLAR CYCLOADDITION; TETRAETHYL VINYLIDENEBISPHOSPHONATE; FUSED HETEROCYCLES; ZOLEDRONIC ACID; DERIVATIVES; MECHANISM; ESTERS; PEPTIDOMIMETICS; PYRAZOLIDINONES; OSTEOPOROSIS;

D O I：

10.1055/s-0036-1591555

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise, atom-economic, and highly regioselective synthetic strategy for the construction of several dinitrogen-fused heterocycles bearing bisphosphonates by 1,3-dipolar cycloaddition reaction of azomethine imines with tetraethyl vinylidene-1,1-bisphosphonate in the presence of CuI in toluene media has been developed. The targeted compounds were obtained in good yields and with excellent regioselectivity. This method for the synthesis of gem-bisphosphonates (BPs) is particularly attractive due to features such as low cost, mild conditions, atom economy, high stereoselectivity, and potential biological activity of the product.

引用

页码：2601 / 2607

页数：7

共 8 条

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Corpas, Javier
Ponce, Alberto
Adrio, Javier
Carretero, Juan C.
ORGANIC LETTERS, 2018, 20 (11) : 3179 - 3182
[2] Acid-Catalyzed [3+2] Cycloaddition of Enones with Azomethine Imines for Easy Access to Tetrahydropyrazolopyrazolones
Jovanovic, Jovana P.
Bogdanovic, Goran A.
Damljanovic, Ivan
SYNLETT, 2017, 28 (06) : 664 - 668
[3] DABCO-catalyzed [3+2] cycloaddition reactions of azomethine imines with N-aryl maleimides: facile access to dinitrogen-fused heterocycles
Jia, Qianfa
Chen, Lei
Yang, Gongming
Wang, Jian
Wei, Jia
Du, Zhiyun
TETRAHEDRON LETTERS, 2015, 56 (52) : 7150 - 7153
[4] Phosphine-Catalyzed [3+2] Cycloaddition Reactions of Azomethine Imines with Electron-Deficient Alkenes: A Facile Access to Dinitrogen-Fused Heterocycles
Li, Zhen
Yu, Hao
Liu, Honglei
Zhang, Lei
Jiang, Hui
Wang, Bo
Guo, Hongchao
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (06) : 1731 - 1736
[5] Pt(II)- or Au(III)-catalyzed [3+2] cycloaddition of metal-containing azomethine ylides: Highly efficient synthesis of the mitosene skeleton
Kusama, H
Miyashita, Y
Takaya, J
Iwasawa, N
ORGANIC LETTERS, 2006, 8 (02) : 289 - 292
[6] Base catalyzed unexpected rearrangement of isatin-derived N,N′-cyclic azomethine imines and Michael addition to hindered vinylidene bisphosphonates: Access to 3,3-disubstituted oxindole-fused pyrazolidin-3-one derivatives containing bisphosphonates
Wang, Qing-He
Zhu, Zhong-Xiang
Huang, Tiao
Wu, Ming-Shu
TETRAHEDRON, 2019, 75 (03) : 416 - 421
[7] R-BINOL-Chiral Phosphoric Acid Catalyzed Regioselective Synthesis of 7-Oxo-Pyrazolo[1,2-a]Pyrazoles via [3+2] Cycloaddition Reaction of Morita Baylis Hillman Adducts with N, N'-Cyclic Azomethine Imines
Karthikeyan, S.
Choppella, Sairathna
Murali, Anna Chandrasekar
Subimol, K. R.
Monica, J. Helen Ratna
Ravva, Mahesh Kumar
Kumar Ayyanoth, Karthik Krishna
CHEMISTRYSELECT, 2024, 9 (27):
[8] Catalyst-free 1,3-dipolar [3+2] cycloadditions of N,N'-cyclic azomethine imines with b-substituted-a,b-unsaturated carbonyls: Access to highly regioselective functionalized N,N'-bicyclic pyrazolidinones
Kang, Sung Hyun
No, Jaeeun
Kim, Sung-Gon
TETRAHEDRON LETTERS, 2023, 120

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