Iron-Catalyzed Stereoselective Synthesis of (Z)-2-Ylidene-1,4-benzodioxanes in the Presence of Cs2CO3

被引:2
作者
Liang, Linfeng [1 ,2 ]
Fang, Qi [1 ]
Xu, Xiaobing [1 ]
Li, Yanzhong [1 ]
机构
[1] E China Normal Univ, Dept Chem, Shanghai 200062, Peoples R China
[2] Shanghai Univ Engn Sci, Shanghai 201620, Peoples R China
关键词
iron catalysis; 1,4-benzodioxane; monopropargyl catechol; selective synthesis; ACIDS; HETEROANNULATION; CYCLIZATION;
D O I
10.6023/cjoc1107111
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of monopropargyl catechol derivatives synthesized via the Sonogashira coupling reaction were stereoselectively converted to (Z)-2-ylidene-1,4-benzodioxanes using FeCl3 as the catalyst, and structurally characterized by H-1 NMR, C-13 NMR and HRMS techniques.
引用
收藏
页码:409 / 412
页数:4
相关论文
共 16 条
[1]   PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES AND VINYL ARYL HALIDES WITH 4-ALKYNOIC ACIDS - REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (E)-DELTA-VINYL ARYL-GAMMA-METHYLENE-GAMMA-BUTYROLACTONES [J].
ARCADI, A ;
BURINI, A ;
CACCHI, S ;
DELMASTRO, M ;
MARINELLI, F ;
PIETRONI, BR .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :976-982
[2]   CONSTITUENTS OF SILYBUM-MARIANUM - STRUCTURE OF ISOSILYBIN AND STEREOCHEMISTRY OF SILYBIN [J].
ARNONE, A ;
MERLINI, L ;
ZANAROTTI, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (16) :696-697
[3]   Palladium mediated regio- and stereoselective synthesis of exomethylene benzo- and naphthodioxans [J].
Basak, A ;
Bhattacharya, G ;
Mallik, UK ;
Khamrai, UK .
SYNTHETIC COMMUNICATIONS, 1997, 27 (03) :367-373
[4]   SYNTHESIS OF POLYETHER CARBOXYLIC-ACIDS WITH A BENZODIOXINIC SUBUNIT [J].
BOSSERAY, P ;
GUILLAUMET, G ;
COUDERT, G ;
WASSERMANN, H .
TETRAHEDRON LETTERS, 1989, 30 (11) :1387-1390
[5]   Palladium-catalyzed heteroannulation leading to heterocyclic structures with two heteroatoms:: A highly convenient and facile method for a totally regio- and stereoselective synthesis of (Z)-2,3-dihydro-2-(ylidene)-1,4-benzo- and -naphtho[2,3-b]dioxins [J].
Chowdhury, C ;
Chaudhuri, G ;
Guha, S ;
Mukherjee, AK ;
Kundu, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :1863-1871
[6]   Palladium-catalyzed heteroannulation of catechol with functionalized propargylic carbonates: Influence of the functional group on the regioselectivity of the cyclization [J].
Dominczak, Norbert ;
Lhoste, Paul ;
Kryczka, Boguslaw ;
Sinou, Denis .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 264 (1-2) :110-118
[7]   Covalent modification of cyclooxygenase-2 (COX-2) by 2-acetoxyphenyl alkyl sulfides, a new class of selective COX-2 inactivators [J].
Kalgutkar, AS ;
Kozak, KR ;
Crews, BC ;
Hochgesang, GP ;
Marnett, LJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (24) :4800-4818
[8]   Palladium-catalyzed annulation of aryl-1,2-diols and propargylic carbonates. Theoretical study of the observed regioselectivities [J].
Labrosse, JR ;
Lhoste, P ;
Delbecq, F ;
Sinou, D .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (15) :2813-2822
[9]   An easy palladium-catalyzed access to 2-alkylidene-1,4-benzodioxanes [J].
Labrosse, JR ;
Lhoste, P ;
Sinou, D .
TETRAHEDRON LETTERS, 1999, 40 (51) :9025-9028
[10]   NEW 1,4-DIHYDROPYRIDINE DERIVATIVES COMBINING CALCIUM ANTAGONISM AND ALPHA-ADRENOLYTIC PROPERTIES [J].
MARCINIAK, G ;
DELGADO, A ;
LECLERC, G ;
VELLY, J ;
DECKER, N ;
SCHWARTZ, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1402-1407