Double decarboxylative Claisen rearrangement reactions:: microwave-assisted de novo synthesis of pyridines

被引：17

作者：

Craig, Donald ^{[1
]}

Paina, Federica ^{[1
]}

Smith, Stephen C. ^{[2
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] Syngenta, Crop Protect Res Chem, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

来源：

CHEMICAL COMMUNICATIONS | 2008年 / 29期

关键词：

D O I：

10.1039/b805078c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Microwave-assisted double decarboxylative Claisen rearrangement of bis(allyl) 2-tosylmalonates provides substituted 1,6-heptadienes, which may be alkylated, and then converted into pyridines by ozonolysis followed by reaction with ammonia generated in situ under microwave conditions.

引用

页码：3408 / 3410

页数：3

共 26 条

[1]

[Anonymous], ALDRICHIMICA ACTA

[2] Potassium hydroxide-mediated novel rearrangement of 2-alkyl-sulfonyl-2-arylsulfonyl-1-phenylethanones to 1-aryl-2-(arylsulfonylmethanesulfonyl)ethanones [J].

Bin, JK ;

Lee, JS ;

Kim, K .

ORGANIC LETTERS, 2004, 6 (23) :4297-4300

[3] A [3,3]-sigmatropic process catalysed by acetate. The decarboxylative Claisen rearrangement [J].

Bourgeois, D ;

Craig, D ;

Grellepois, F ;

Mountford, DM ;

Stewart, AJW .

TETRAHEDRON, 2006, 62 (2-3) :483-495

[4] Synthesis of homoallylic sulfones through a decarboxylative Claisen rearrangement reaction [J].

Bourgeois, D ;

Craig, D ;

King, NP ;

Mountford, DM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :618-621

[5] Claisen rearrangement over the past nine decades [J].

Castro, AMM .

CHEMICAL REVIEWS, 2004, 104 (06) :2939-3002

[6] New aspects of the Ireland and related Claisen rearrangements [J].

Chai, YH ;

Hong, SP ;

Lindsay, HA ;

McFarland, C ;

McIntosh, MC .

TETRAHEDRON, 2002, 58 (15) :2905-2928

[7] First total synthesis of (±)-prelunularin [J].

Comas, H ;

Pandolfi, E .

SYNTHESIS-STUTTGART, 2004, (15) :2493-2498

[8] Heteroaromatic decarboxylative claisen rearrangement reactions [J].

Craig, D ;

King, NP ;

Kley, JT ;

Mountford, DM .

SYNTHESIS-STUTTGART, 2005, (19) :3279-3282

[9] Asymmetric decarboxylative Claisen rearrangement reactions of sulfoximine-substituted allylic tosylacetic esters [J].

Craig, D ;

Grellepois, F ;

White, AJP .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6827-6832

[10] Sulfone-mediated synthesis of polysubstituted pyridines [J].

Craig, D ;

Henry, GD .

TETRAHEDRON LETTERS, 2005, 46 (15) :2559-2562

← 1 2 3 →