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

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 01期

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

页码：115 / 118

页数：4

共 53 条

[1] Electrophilic cyclization of o-acetoxy- and o-benzyloxyalkynylpyridines:: An easy entry into 2,3-disubstituted furopyridines [J].

Arcadi, A ;

Cacchi, S ;

Di Giuseppe, S ;

Fabrizi, G ;

Marinelli, F .

ORGANIC LETTERS, 2002, 4 (14) :2409-2412

[2] A NEW SYNTHESIS OF 4,5,6,7-TETRAHYDROFURO[2,3-C]PYRIDINES AND FURO[2,3-C]PYRROLIDINES [J].

ARNOLDI, A ;

BREGANTE, G ;

CALDIROLA, P ;

MERLINI, L ;

TAMBURINI, B .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (05) :1169-1171

[3]

BERTIN J, 1990, Patent No. 358558

[4] A PRACTICAL SYNTHESIS OF 5-(CHLOROMETHYL)FURO[2,3-B]PYRIDINE, A KEY INTERMEDIATE FOR THE HIV PROTEASE INHIBITOR, L-754,394 [J].

BHUPATHY, M ;

CONLON, DA ;

WELLS, KM ;

NELSON, JR ;

REIDER, PJ ;

ROSSEN, K ;

SAGER, JW ;

VOLANTE, RP ;

DORSEY, BD ;

HOFFMAN, JM ;

JOSEPH, SA ;

MCDANIEL, SL .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (04) :1283-1287

[5]

Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO

[6]

2-A

[7] Palladium-mediated three-component synthesis of furo[2,3-b]pyridones by one-pot coupling of 3-lodopyridones, alkynes, and organic halides [J].

Bossharth, E ;

Desbordes, P ;

Monteiro, N ;

Balme, G .

ORGANIC LETTERS, 2003, 5 (14) :2441-2444

[8] PSORALENS AS PHOTOACTIVE PROBES OF NUCLEIC-ACID STRUCTURE AND FUNCTION - ORGANIC-CHEMISTRY, PHOTOCHEMISTRY, AND BIOCHEMISTRY [J].

CIMINO, GD ;

GAMPER, HB ;

ISAACS, ST ;

HEARST, JE .

ANNUAL REVIEW OF BIOCHEMISTRY, 1985, 54 :1151-1193

[9] A rapid access to biaryl ether containing macrocycles by pairwise use of Ugi 4CR and intramolecular SNAr-based cycloetherification [J].

Cristau, P ;

Vors, JP ;

Zhu, JP .

ORGANIC LETTERS, 2001, 3 (25) :4079-4082

[10]

Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO

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