Modular, Concise, and Efficient Synthesis of Highly Functionalized 5-Fluoropyridazines by a [2+1]/[3+2]-Cycloaddition Sequence

被引：25

作者：

Tran, Gael ^{[1
]}

Pardo, Domingo Gomez ^{[1
]}

Tsuchiya, Tomoki ^{[1
]}

Hillebrand, Stefan ^{[1
]}

Vors, Jean-Pierre ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] PSL Res Univ, ESPCI ParisTech, Inst Chem Biol & Innovat CBI, Lab Chim Organ,UMR 8231, F-75231 Paris 05, France

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 14期

关键词：

DIAZO-COMPOUNDS; CYCLOPROPANES; ISOMERIZATION; DIAZOALKANES; PYRIDAZINES; KETONES; MONO;

D O I：

10.1021/acs.orglett.5b01370

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An easy access to 5-fluoropyridazines by a [2 + 1]/[3 + 2]-cydoaddition sequence between terminal alkynes, a difluorocarbene, and a diazo compound is reported. This approach does not necessitate the isolation of any intermediates, and a wide range Of novel 5-fluoropyridazines was synthesized from readily available starting materials. Additionally, these compounds were used as a platform to access novel and highly diversified pyridazines.

引用

页码：3414 / 3417

页数：4

共 50 条

[1] Catalytic asymmetric synthesis of highly functionalized cyclopentenes by a [3+2] cycloaddition
Davies, HML
Xiang, BP
Kong, N
Stafford, DG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) : 7461 - 7462
[2] A Regio- and Diastereoselective Platinum-Catalyzed Tandem [2+1]/[3+2] Cycloaddition Sequence
Achard, Thierry
Lepronier, Aymeric
Gimbert, Yves
Clavier, Herve
Giordano, Laurent
Tenaglia, Alphonse
Buono, Gerard
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (15) : 3552 - 3556
[3] Highly Efficient Asymmetric [3+2] Cycloaddition Promoted by Chiral Aziridine-Functionalized Organophosphorus Compounds
Szymanska, Julia
Rachwalski, Michal
Pieczonka, Adam M.
[J]. MOLECULES, 2024, 29 (14):
[4] Gold catalysis: up to six new bonds by a domino [3+2]/[2+1]/[2+1] cycloaddition
Conyers, Ryan C.
Barnes, Charles L.
Gung, Benjamin W.
[J]. TETRAHEDRON LETTERS, 2015, 56 (23) : 3318 - 3321
[5] Stereoselective Synthesis of Highly Functionalized Dispirooxindoles through [3+2] Cycloaddition of Carbonyl Ylides with 3-Arylideneoxindoles
Reddy, Basi V. Subba
Karthik, Govindaraju
Rajasekaran, Tamilselvan
Sridhar, Balasubramanian
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (09) : 2038 - 2041
[6] Highly efficient [2+1] cycloaddition reactions of a 1-seleno-2-silylethene to 2-phosphonoacrylates: Synthesis of novel functionalized cyclopropanephosphonic acid esters.
Yamazaki, S
Imanishi, T
Moriguchi, Y
Takada, T
[J]. TETRAHEDRON LETTERS, 1997, 38 (36) : 6397 - 6400
[7] A [3+2] - [4+2] - [3+2] cycloaddition sequence of isoquinolinium ylide
Liu, Ruzhang
Shi, Rong-Guo
Sun, Jing
Yan, Chao-Guo
[J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (03): : 354 - 357
[8] Sequential [3+2] cycloaddition/reaffangement reaction of imidazolone nitrones and allenoates for the efficient synthesis of functionalized imidazolidinone
Wu, Xi
Na, Risong
Liu, Honglei
Liu, Jun
Wang, Min
Zhong, Jiangchun
Guo, Hongchao
[J]. TETRAHEDRON LETTERS, 2012, 53 (03) : 342 - 344
[9] Sequential (3+2) cycloaddition and (5+n) annulation for modular synthesis of dihydrobenzoxazines, tetrahydrobenzoxazepines and tetrahydrobenzoxazocines
Muthengi, Alex
Zhang, Xiaofeng
Dhawan, Gagan
Zhang, Wensheng
Corsini, Francesca
Zhang, Wei
[J]. GREEN CHEMISTRY, 2018, 20 (13) : 3134 - 3139
[10] Concise synthesis of the core structure of madreporanone by Rh-catalyzed [3+2] cycloaddition
Long, Rong
Yang, Zhen
[J]. TETRAHEDRON, 2019, 75 (12) : 1746 - 1750

← 1 2 3 4 5 →