Multicomponent Syntheses to Alkene- and Alkyne-Functionalized Benzopyrans via Alkynylation and [4+2] Cyclization in One-Pot Process

被引:4
作者
Shao, Jidong
Li, Liqi
Zhang, Jie
Tian, Tian
Xue, Jijun [1 ]
Zhang, Yuan
Li, Ying
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
关键词
one-pot; multicomponent; alkynylation; 4+2] cyclization; benzopyran; PRIVILEGED STRUCTURES; COMBINATORIAL LIBRARIES; MURRAYA EUCHRESTIFOLIA; CATALYZED CYCLIZATION; QUINONE METHIDES; CHROMANS; CHEMISTRY; CASCADE; SALICYLALDEHYDES; CYCLOADDITION;
D O I
10.1055/s-0034-1380118
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel multicomponent synthesis was found to be an efficient and elegant approach to 2,4-difunctionalized benzopyrans. This sequence includes ZnMe2-promoted alkynylation of salicylaldehyde and ZnCl2-mediated [4+2] cyclization proceeding in sequence of a one-pot process, providing a series of benzopyrans with good diastereoselectivities and moderate yields (dr 20:1 to 4:1). These products are potential precursors and bioactive core skeletons of natural products.
引用
收藏
页码:827 / 833
页数:7
相关论文
共 39 条
[11]   Traceless stereoinduction in the one-pot assembly of all three rings of hexahydrodibenzopyrans [J].
Korthals, Keith A. ;
Wulff, William D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (10) :2898-2899
[12]   Enantioselective synthesis of the tetrahydro-6H-benzo[c]chromenes via Domino Michael-Aldol condensation: control of five stereocenters in a quadruple-cascade organocatalytic multi-component reaction [J].
Kotame, Prakash ;
Hong, Bor-Cherng ;
Liao, Ju-Hsiou .
TETRAHEDRON LETTERS, 2009, 50 (06) :704-707
[13]  
KUREEL SP, 1969, TETRAHEDRON LETT, P3857, DOI 10.1016/S0040-4039(01)88531-2
[14]   Copper(I)-Catalyzed Hydroalkoxylation/Hydrogen-Bonding-Induced Asymmetric Hetero-Diels-Alder Cycloaddition Cascade: An Approach to Aromatic Spiroketals [J].
Li, Xin ;
Xue, Jijun ;
Huang, Chusheng ;
Li, Ying .
CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (05) :903-906
[15]   Highly enantioselective addition of phenylacetylene to ketones catalyzed by bis(hydroxycamphorsulfonamide)-copper(II) complex [J].
Liu, Lei ;
Wang, Rui ;
Kang, Yong-Feng ;
Cai, Hua-Qing ;
Chen, Chao .
SYNLETT, 2006, (08) :1245-1249
[16]   Regio- and diastereoselective insertion of allenes into stable oxapalladacycles with a metal-bonded stereogenic carbon.: Preparation of contiguously substituted 3,4-dihydro-2H-1-benzopyrans [J].
Lu, GL ;
Malinakova, HC .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) :8266-8279
[17]   PPh3-Catalyzed Domino Reaction: A Facile Method for the Synthesis of Chroman Derivatives [J].
Meng, Xiangtai ;
Huang, You ;
Zhao, Hongxia ;
Xie, Peizhong ;
Ma, Jianze ;
Chen, Ruyu .
ORGANIC LETTERS, 2009, 11 (04) :991-994
[18]   BF3•Et2O-mediated cascade cyclizations:: Synthesis of schweinfurthins F and G [J].
Mente, Nolan R. ;
Neighbors, Jeffrey D. ;
Wiemer, David F. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20) :7963-7970
[19]   Asymmetric chroman synthesis via an intramolecular oxy-Michael addition by bifunctional organocatalysts [J].
Miyaji, Ryota ;
Asano, Keisuke ;
Matsubara, Seijiro .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (01) :119-122
[20]   Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans [J].
Nicolaou, KC ;
Pfefferkorn, JA ;
Roecker, AJ ;
Cao, GQ ;
Barluenga, S ;
Mitchell, HJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) :9939-9953