Palladium-Catalyzed Oxidative Cyclization of Azulene-2-Carboxylic Acids with 1,3-Dienes for the Synthesis of Alkenyl Azulenolactones

被引:4
作者
Maeng, Chanyoung [1 ]
Yun, Yongjoo [1 ]
Son, Jeong-Yu [1 ]
Lee, Phil Ho [1 ]
机构
[1] Kangwon Natl Univ, Dept Chem, Chunchon 24341, South Korea
基金
新加坡国家研究基金会;
关键词
palladium; C-H activation; azulene; 1; 3-diene; azulenolactone; EXPANSION-ANNULATION STRATEGY; ELECTRON-RICH ARENES; SUBSTITUTED AZULENES; BOND ACTIVATION; ACCESS; ARYLATION; ROUTE; HYDROARYLATION; DERIVATIVES; CASCADE;
D O I
10.1002/adsc.202200452
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We have developed Pd-catalyzed oxidative cyclization reactions of a wide range of azulene-2-carboxylic acids with a large number of activated as well as unactivated 1,3-dienes, consequently allowing a streamlined synthetic method for the selective preparation of monosubstituted alkenyl dihydroazulenolactones and their derivatives.
引用
收藏
页码:2859 / 2864
页数:6
相关论文
共 67 条
[1]   Organogold(III) iminophosphorane complexes as efficient catalysts in the addition of 2-methylfuran and electron-rich arenes to methyl vinyl ketone [J].
Aguilar, David ;
Contel, Maria ;
Navarro, Rafael ;
Urriolabeitia, Esteban P. .
ORGANOMETALLICS, 2007, 26 (18) :4604-4611
[2]   Stimuli-Responsive Azulene-Based Conjugated Oligomers with Polyaniline-like Properties [J].
Amir, Elizabeth ;
Amir, Roey J. ;
Campos, Luis M. ;
Hawker, Craig J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (26) :10046-10049
[3]  
[Anonymous], 2005, ANGEW CHEM, V117, P5260
[4]  
[Anonymous], 2017, ANGEW CHEM
[5]   Benzo[cd]azulene Skeleton: Azulene, Heptafulvene, and Tropone Derivatives [J].
Aumuller, Ingo B. ;
Yli-Kauhaluoma, Jari .
ORGANIC LETTERS, 2009, 11 (23) :5363-5365
[6]   Synthesis of Quinolizinones from Rhodium-Catalyzed C-H Activation Reaction of 2-(1-Cycloalkenyl)pyridines with Diazo Meldrum's Acids [J].
Baek, Yonghyeon ;
Kim, Ya Gob ;
Lee, Phil Ho .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2021, 42 (03) :495-498
[7]   A NEW SYNTHESIS OF SUBSTITUTED AZULENES [J].
BECKER, DA ;
DANHEISER, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (01) :389-391
[8]   Au-Catalyzed Cross-Coupling of Arenes via Double C-H Activation [J].
Cambeiro, Xacobe C. ;
Ahlsten, Nanna ;
Larrosa, Igor .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (50) :15636-15639
[9]   Approach to the blues:: A highly flexible route to the azulenes [J].
Carret, S ;
Blanc, A ;
Coquerel, Y ;
Berthod, M ;
Greene, AE ;
Deprés, JP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (32) :5130-5133
[10]   Ruthenium(II)-Catalyzed C-H/N-H Carbonylative Cyclization of 2-Aryl Quinazolinones with Isocyanates as CO Surrogates [J].
Choi, Jin Ho ;
Do Kim, Hak ;
Kang, Ju Young ;
Jeong, Taejoo ;
Ghosh, Prithwish ;
Kim, In Su .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2021, 42 (03) :542-547