Facile Synthesis of Coumarin- and Quinolone-Annulated Benzazoninone Derivatives by an Intramolecular Heck Reaction Strategy via 9-exo-trig Cyclization

被引：12

作者：

Majumdar, K. C. ^{[1
]}

Ghosh, Tapas ^{[1
]}

Samanta, Srikanta ^{[1
]}

机构：

[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India

来源：

SYNTHESIS-STUTTGART | 2011年 / 10期

关键词：

coumarin; quinolone; benzazoninones; aza-Claisen rearrangement; Heck reaction; 9-MEMBERED RING LACTAMS; OPTICALLY-ACTIVE AZONINONES; QUATERNARY CARBON CENTERS; TRANSANNULAR REACTIONS; 3-AZA-COPE REARRANGEMENT; CYCLIC CARBOPALLADATION; PLANAR CHIRALITY; INDOLIZIDINE; METHODOLOGY; INVERSION;

D O I：

10.1055/s-0030-1260005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic strategy based on the application of the aromatic aza-Claisen rearrangement followed by an intramolecular Heck reaction sequence as the key step has been developed for the regiocontrolled synthesis of hitherto unreported coumarin- and quinolone-annulated benzazoninone derivatives in 48-69% yield.

引用

页码：1569 / 1574

页数：6

共 12 条

[1] Synthesis of Coumarin- and Quinolone-Annulated Benzazocinone Frameworks by a Palladium-Catalyzed Intramolecular Heck Reaction
Majumdar, K. C.
Samanta, Srikanta
Ghosh, Tapas
[J]. SYNTHESIS-STUTTGART, 2012, 44 (11): : 1711 - 1717
[2] Regioselective synthesis of coumarin and quinolone-annulated linearly fused heterocycles by the intramolecular Heck reaction of the biaryl systems
Majumdar, Krishna C.
Chattopadhyay, Buddhadeb
Pal, Amarta K.
[J]. LETTERS IN ORGANIC CHEMISTRY, 2008, 5 (04) : 276 - 281
[3] Regioselective synthesis of coumarin and quinolone-annulated spiro heterocycles via aryl radical cyclization
Majumdar, KC
Mukhopadhyay, PP
Basu, PK
[J]. SYNTHETIC COMMUNICATIONS, 2005, 35 (10) : 1291 - 1299
[4] Highly effective regioselective method for the synthesis of substituted coumarin- and quinolone-annulated heterocycles using a palladium(0)-catalyzed reaction
Majumdar, K. C.
Pal, A. K.
Taher, A.
Debnath, P.
[J]. SYNTHESIS-STUTTGART, 2007, (11): : 1707 - 1711
[5] A new strategy for the synthesis of coumarin- and quinolone-annulated pyrroles via Pd(0) mediated cross-coupling followed by Cu(I) catalyzed heteroannulation
Majumdar, K. C.
Mondal, Shovan
[J]. TETRAHEDRON LETTERS, 2008, 49 (15) : 2418 - 2420
[6] Synthesis of highly substituted dibenzoazocine derivatives by the aza-Claisen rearrangement and intramolecular Heck reaction via 8-exo-trig mode of cyclization
Majumdar, K. C.
Chattopadhyay, Buddhadeb
Samanta, Srikanta
[J]. TETRAHEDRON LETTERS, 2009, 50 (26) : 3178 - 3181
[7] An efficient synthesis of coumarin- and quinolone-annulated thiazole derivatives via ligand-free iron (III)-catalyzed coupling followed by acid-promoted condensation
Majumdar, K. C.
Ghosh, Debankan
[J]. TETRAHEDRON LETTERS, 2013, 54 (33) : 4422 - 4424
[8] Novel synthesis of oxocine derivatives by Wittig olefination and intramolecular Heck reaction via 8-endo trig cyclization
Majumdar, K. C.
Chattopadhyay, B.
Sinha, B.
[J]. TETRAHEDRON LETTERS, 2008, 49 (08) : 1319 - 1322
[9] Novel Synthesis of Oxathiocine Derivatives by Wittig Olefination and Intramolecular Heck Reaction via an 8-endo-trig Cyclization
Majumdar, Krishna C.
Chattopadhyay, Buddhadeb
Sinha, Biswajit
[J]. SYNTHESIS-STUTTGART, 2008, (23): : 3857 - 3863
[10] A Green Synthesis of Angularly Fused Furano-Pyrone/Coumarin and Quinolone Derivatives via Molecular Iodine-Mediated 5-exo-trig Cyclization in Aqueous Micelles
Majumdar, K. C.
Ghosh, Debankan
Mondal, Shovan
[J]. SYNTHESIS-STUTTGART, 2011, (04): : 599 - 602

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