Synthesis of polysubstituted 4,5,6,7-tetrahydrofuro[2,3-c]pyridines by a novel multicomponent reaction

被引:69
作者
Fayol, A [1 ]
Zhu, JP [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1021/ol036167p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel three-component synthesis of tetrahydrofuro[2,3-c]pyridines (1) from readily accessible starting materials is described. Simply heating a toluene solution of an aminopentynoate (2a), an aldehyde (3), and an alpha-isocyanoacetamide (4) in the presence of ammonium chloride provided the 4,5,6,7-tetrahydrofuro[2,3-c]pyridines (1) in good to excellent yield. The fused ring system is produced in this one-pot process by the concomitant formation of five chemical bonds.
引用
收藏
页码:115 / 118
页数:4
相关论文
共 53 条
[31]  
2-9
[32]   SYNTHESIS OF FURO[2,3-C]PYRIDINE DERIVATIVES [J].
MERTES, MP ;
BORNE, RF ;
HARE, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) :133-&
[33]   Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds [J].
Orru, RVA ;
de Greef, M .
SYNTHESIS-STUTTGART, 2003, (10) :1471-1499
[34]   Teubrevin G and Teubrevin H:: The first total syntheses of rearranged neo-clerodanes including solutions to the problems of chirality merger and furan ring assembly [J].
Paquette, LA ;
Efremov, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4492-4501
[35]  
Rostovtsev VV, 2002, ANGEW CHEM INT EDIT, V41, P2596, DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO
[36]  
2-4
[37]   ACID-CATALYZED CYCLIZATION OF 1-ARYL-2-THIENYLMETHYL-AMINDETHANOLS AND 1-ARYL-2-FURFURYL-AMINOETHANOLS VIA SPIRO INTERMEDIATES [J].
SCHNEIDER, CS ;
POOK, KH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (06) :877-883
[38]  
SHIOTANI S, 1986, J HETEROCYCLIC CHEM, V23, P233
[39]  
SHIOTANI S, 1997, HETEROCYCLES, V975
[40]   A novel multicomponent synthesis of polysubstituted 5-aminooxazole and its new scaffold-generating reaction to pyrrolo[3,4-b]pyridine [J].
Sun, XW ;
Janvier, P ;
Zhao, G ;
Bienaymé, H ;
Zhu, JP .
ORGANIC LETTERS, 2001, 3 (06) :877-880