New and efficient RCM in pyridinic series:: synthesis of 2H-dihydropyrano- or 2,3H-dihydrooxepino[3,2-b]pyridines

被引：15

作者：

Banaszak, Estelle ^{[1
]}

Comoy, Corinne ^{[1
]}

Fort, Yves ^{[1
]}

机构：

[1] Univ Nancy 1, CNRS, UMR 7565, Fac Sci & Tech, F-54506 Vandoeuvre Les Nancy, France

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 35期

关键词：

2H-dihydropyrano[3,2-b]pyridine; 2,3H-dihydrooxepino[3,2-b]pyridine; Stille cross coupling; RCM reaction;

D O I：

10.1016/j.tetlet.2006.06.139

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and very efficient route to polycyclic heterocycles with isosteric replacement of benzene by pyridine is reported. This strategy involving the RCM reaction in pyridinic series as a keystep allows us to prepare 2H-dihydropyrano- or 2,3H-dihydrooxepino[3,2-b]pyridines I and 2 in very good overall yields (47% and 44%, respectively). (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：6235 / 6238

页数：4

共 31 条

[1] Synthesis of coumarins in a molten n-Bu4NOAc/n-Bu4NBr mixture through a domino Heck reaction/cyclization process [J].

Battistuzzi, G ;

Cacchi, S ;

De Salve, I ;

Fabrizi, G ;

Parisi, LM .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :308-312

[2]

BILLERET D, 1993, SYNTHESIS-STUTTGART, P881

[3] SYNTHESIS OF FUNDAMENTAL HETEROCYCLES C5O-C5N - 2H-PYRANO[3,2-B]-PYRIDINE AND 2H-PYRANO[2,3-C]PYRIDINE [J].

BILLERET, D ;

BLONDEAU, D ;

SLIWA, H .

TETRAHEDRON LETTERS, 1991, 32 (05) :627-628

[4]

BOHN B, 1994, HETEROCYCLES, V37, P1731

[5] Ring-closing metathesis approach to symmetrical and unsymmetrical cycloakeno[c]fused 2,2′-bipyridine-based cyclophanes [J].

Branowska, D ;

Rykowski, A .

TETRAHEDRON, 2005, 61 (45) :10713-10718

[6]

BRIDGER G, 2002, Patent No. [0222600, 00222600]

[7] CLAISEN REARRANGEMENT OF 2-PROPINYL (3-PYRIDYL) AND ALLYL (3-PYRIDYL)ETHERS [J].

BRUHN, J ;

ZSINDELY, J ;

SCHMID, H .

HELVETICA CHIMICA ACTA, 1978, 61 (07) :2542-2559

[8] A highly efficient and practical synthesis of chromene derivatives using ring-closing olefin metathesis [J].

Chang, SB ;

Grubbs, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) :864-866

[9] Synthesis and regioselective alkylation of 1,6-and 1,7-naphthyridines [J].

Colandrea, VJ ;

Naylor, EM .

TETRAHEDRON LETTERS, 2000, 41 (42) :8053-8057

[10] New efficient access to thieno[3,2-b]pyridine derivatives via regioselective lithiation of 3-methylthiopyridine [J].

Comoy, Corinne ;

Banaszak, Estelle ;

Fort, Yves .

TETRAHEDRON, 2006, 62 (25) :6036-6041

← 1 2 3 4 →