Synthesis of N-heterocyclic compounds via ene-yne metathesis reactions

被引：24

作者：

Groaz, Elisabetta ^{[1
]}

Banti, Donatella ^{[1
,2
]}

North, Michael ^{[1
,3
]}

机构：

[1] Kings Coll London, Dept Chem, London WC2R 2LS, England

[2] Kingston Univ, Sch Pharm & Chem, Kingston upon Thames KT1 2EE, Surrey, England

[3] Univ Newcastle, Sch Nat Sci, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

TETRAHEDRON | 2008年 / 64卷 / 01期

关键词：

nitrogen heterocycles; ring closing; enyne; metathesis; ruthenium;

D O I：

10.1016/j.tet.2007.10.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Propargylamino and allylamino derivatives of cyclohexene and norbornene were subjected to tandem metathesis reactions with first and second generation Grubbs' catalysts 1 and 2. Results show that the method is compatible with suitably protected nitrogen-containing compounds. Cyclohexenes gave intriguing results in terms of the possibility to perform ring rearrangement metathesis (RRM) reactions, showing a difference with the analogous allyl and propargyl ether substrates. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：204 / 218

页数：15

共 84 条

[1] Concise synthesis of azacycloundecenes using ring-closing metathesis (RCM)
Arisawa, M
Kato, C
Kaneko, H
Nishida, A
Nakagawa, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12): : 1873 - 1876
[2] Preparation of nitrogen-containing heterocycles using ring-closing metathesis (RCM) and its application to natural product synthesis
Arisawa, Mitsuhiro
Nishida, Atsushi
Nakagawa, Masako
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (24-25) : 5109 - 5121
[3] Lewis-acid assisted cross metathesis of acrylonitrile with functionalized olefins catalyzed by phosphine-free ruthenium carbene complex
Bai, CX
Lu, XB
He, R
Zhang, WZ
Feng, XJ
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (22) : 4139 - 4142
[4] Ene-yne metathesis of polyunsaturated norbornene derivatives
Banti, D
Groaz, E
North, M
[J]. TETRAHEDRON, 2004, 60 (37) : 8043 - 8052
[5] Ene-yne-ene and ene-yne-yne metathesis of norbornene derivatives
Banti, D
North, M
[J]. TETRAHEDRON LETTERS, 2003, 44 (44) : 8157 - 8160
[6] Banti D, 2002, ADV SYNTH CATAL, V344, P694, DOI 10.1002/1615-4169(200208)344:6/7<694::AID-ADSC694>3.0.CO
[7] 2-X
[8] Totally atom economical tandem-metathesis and Diels-Alder approach to polycyclic compounds
Banti, D
North, M
[J]. TETRAHEDRON LETTERS, 2002, 43 (08) : 1561 - 1564
[9] EXPERIMENTAL STUDIES OF THE ANOMERIC EFFECT .2. RING INVERSION AND NITROGEN INVERSION EQUILIBRIA IN CIS- DECAHYDROQUINAZOLINES
BOOTH, H
KHEDHAIR, KA
ALSHIRAYDA, HARY
[J]. TETRAHEDRON, 1988, 44 (05) : 1465 - 1475
[10] Synthesis of cyclic peptidosulfonamides by ring-closing metathesis
Brouwer, AJ
Liskamp, RMJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11) : 3662 - 3668

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