Palladium-Catalyzed Three-Component Reaction of Enol Ethers, Salicylaldehyde, and Trimethyl Orthoformate: A Fast Synthesis of Tetrahydro-2H,5H-Pyrano[2,3-b]Chromenes

被引:0
作者
Cordova-Rodriguez, Melina D. [1 ]
Olivares-Castillo, Jose A. [1 ]
Flores-Alamo, Marcos [1 ]
Garcia-Santos, William H. [1 ]
Iglesias-Arteaga, Martin A. [1 ]
机构
[1] Univ Nacl Autonoma Mexico, Fac Quim, Ciudad Univ, Mexico City, Mexico
关键词
NMR; steroids; Tetrahydro-2H,5H-pyrano[2,3-b]chromenes; three-component reactions; X-ray structures; MULTICOMPONENT REACTIONS;
D O I
10.1002/jhet.4949
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Pd-catalyzed three-component reaction of enol ethers, methyl orthoformate, and salicylaldehyde is described. Both steroid and non-steroid enol ethers are compatible. This reaction allows the construction of tetrahydro-2H,5H-pyrano[2,3-b]chromene. Unambiguous NMR characterization and X-ray diffraction structures are provided.
引用
收藏
页码:378 / 382
页数:5
相关论文
共 16 条
[1]   Alkyl Enol Ethers: Development in Intermolecular Organic Transformation [J].
Ahmad, Sarwat Asma Ziya ;
Jena, Tapan Kumar ;
Khan, Faiz Ahmed .
CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (13) :1685-1702
[2]   The Domestication of ortho-Quinone Methides [J].
Bai, Wen-Ju ;
David, Jonathan G. ;
Feng, Zhen-Gao ;
Weaver, Marisa G. ;
Wu, Kun-Liang ;
Pettus, Thomas R. R. .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (12) :3655-3664
[3]   Recent advances in multicomponent reactions for diversity-oriented synthesis [J].
Biggs-Houck, James E. ;
Younai, Ashkaan ;
Shaw, Jared T. .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (03) :371-382
[4]   Chemistry and Biology Of Multicomponent Reactions [J].
Domling, Alexander ;
Wang, Wei ;
Wang, Kan .
CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135
[5]   Diastereodivergent Synthesis of A-Ring Lactones Derived from Cholesterol and Diosgenin: A Convenient Solution for an Old Problem - NMR and X-ray Characterization [J].
Garcia-Santos, William H. ;
Valente-Valdovinos, Paola ;
Cortina-Mendoza, Alvaro J. ;
Flores-Alamo, Marcos ;
Iglesias-Arteaga, Martin A. .
SYNTHESIS-STUTTGART, 2024, 56 (19) :3027-3036
[6]   Mechanistic Insights on Pd-Catalyzed Three-Component Reactions of Alkynols, Methyl Orthoformate, and Salicylaldehyde Derivatives. Application to the Synthesis of Steroid Chroman Ketals and Spiroketals with Antioxidant Activity [J].
Garcia-Santos, William H. ;
Mayorquin-Torres, Martha C. ;
Maldonado-Dominguez, Mauricio ;
Medina-Campos, Omar N. ;
Pedraza-Chaverri, Jose ;
Iglesias-Arteaga, Martin A. .
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (21) :14860-14873
[7]   Rapid syntheses of benzopyrans from o-OBOC salicylaldehydes and salicyl alcohols:: A three-component reaction [J].
Jones, RM ;
Selenski, C ;
Pettus, TRR .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :6911-6915
[8]   Diastereoselective syntheses of chroman spiroketals via [4+2] cycloaddition of enol ethers and o-quinone methides [J].
Marsini, Maurice A. ;
Huang, Yaodong ;
Lindsey, Christopher C. ;
Wu, Kun-Liang ;
Pettus, Thomas R. R. .
ORGANIC LETTERS, 2008, 10 (07) :1477-1480
[9]   Palladium-Catalyzed Generation of ortho-Quinone Methides. A Three-Component Synthesis of L-Shaped Dimeric Steroidal Scaffolds [J].
Mayorquin-Torres, Martha C. ;
Navarro-Huerta, Armando ;
Maldonado-Dominguez, Mauricio ;
Flores-Alamo, Marcos ;
Rodriguez-Molina, Braulio ;
Iglesias-Arteaga, Martin A. .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (05) :4112-4120
[10]   An unexpected course of a palladium catalyzed three-component reaction leading to steroid chroman ketals [J].
Mayorquin-Torres, Martha C. ;
Flores-Alamo, Marcos ;
Iglesias-Arteaga, Martin A. .
TETRAHEDRON LETTERS, 2017, 58 (36) :3500-3504