Diels-Alder approach to biaryls (DAB):: Importance of the ortho-nitro moiety in the [4+2] cycloaddition

被引：17

作者：

Ashburn, Bradley O. ^{[1
]}

Carter, Rich G. ^{[1
]}

机构：

[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 02期

关键词：

D O I：

10.1039/b714893c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of nitrophenyl acetylenes were evaluated for their utility in a cycloaddition-cycloreversion approach to poly-substituted biaryls. ortho-Nitrophenyl acetylene consistently provided the target biaryls in superior yields as compared to the meta and para nitro substituted variants.

引用

页码：255 / 257

页数：3

共 30 条

[1] Novel P2X7 receptor antagonists [J].

Alcaraz, L ;

Baxter, A ;

Bent, J ;

Bowers, K ;

Braddock, M ;

Cladingboel, D ;

Donald, D ;

Fagura, M ;

Furber, M ;

Laurent, C ;

Lawson, M ;

Mortimore, M ;

McCormick, M ;

Roberts, N ;

Robertson, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (22) :4043-4046

[2] GENERATION OF ARYL RADICALS BY THE OXIDATION OF ALPHA-(ARYLAZO)TRIPHENYLMETHANES BY CERIUM(IV) AMMONIUM-NITRATE [J].

ARAI, N ;

NARASAKA, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (06) :1707-1714

[3]

ASHBURN BO, TETRAHEDRON, DOI DOI 10.1016/J.TET/2007/10/118

[4] Diels-Alder approach to tetra-ortho-substituted biaryls employing propargylic tertiary alcohols as dienophiles [J].

Ashburn, Bradley O. ;

Carter, Rich G. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (26) :10220-10223

[5] Synthesis of tetra-ortho-substituted, phosphorus-containing and carbonyl-containing biaryls utilizing a diels-alder approach [J].

Ashburn, Bradley O. ;

Carter, Rich G. ;

Zakharov, Lev N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (29) :9109-9116

[6] Diels-Alder approach to polysubstituted biaryls: Rapid entry to tri- and tetra-ortho-substituted phosphorus-containing biaryls [J].

Ashburn, Bradley O. ;

Carter, Rich G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) :6737-6741

[7]

AVENOZA A, 1995, SYNTHESIS-STUTTGART, P671

[8] Inverse-electron-demand Diels-Alder reactions of 4-aryl-2-pyrones with electron-rich dienophiles [J].

Balázs, L ;

Kádas, I ;

Toke, L .

TETRAHEDRON LETTERS, 2000, 41 (39) :7583-7587

[9] SYNTHESES AND PROPERTIES OF ARENEDIAZONIUM AND ANILINIUM CATION LARIAT ETHER COMPLEXES - AN OSTRICH MOLECULE COMPLEX AND EVIDENCE FOR INTRAMOLECULAR SIDEARM - MACRORING INTERACTION [J].

BEADLE, JR ;

DISHONG, DM ;

KHANNA, RK ;

GOKEL, GW .

TETRAHEDRON, 1984, 40 (20) :3935-3944

[10] INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF HETEROCYCLIC AZADIENES - FORMAL TOTAL SYNTHESIS OF STREPTONIGRIN [J].

BOGER, DL ;

PANEK, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (20) :5745-5754

← 1 2 3 →