Exploiting the Electrophilic and Nucleophilic Dual Role of Nitrile Imines: One-Pot, Three-Component Synthesis of Furo[2,3-d]pyridazin-4(5H)-ones

被引：19

作者：

Giustiniano, Mariateresa ^{[1
]}

Mercalli, Valentina ^{[2
]}

Amato, Jussara ^{[1
]}

Novellino, Ettore ^{[1
]}

Tron, Gian Cesare ^{[2
]}

机构：

[1] Univ Naples Federico II, Dipartimento Farm, Via D Montesano 49, I-80131 Naples, Italy

[2] Univ Piemonte Orientale, Dipartimento Sci Farmaco, I-28100 Novara, Italy

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 16期

关键词：

MULTICOMPONENT REACTIONS; CARDIOTONIC AGENTS; DERIVATIVES; PYRIDAZIN-3(2H)-ONES; HETEROCYCLES; MACROCYCLES; ISOCYANIDES; PYRIDAZINE; CHEMISTRY; CHLORIDES;

D O I：

10.1021/acs.orglett.5b01798

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expeditious multicomponent reaction to synthesize tetrasubstituted furo[2,3-d]pyridazin-4(5H)-ones is reported. In brief, hydrazonoyl chlorides react with isocyanoacetamides, in the presence of TEA, to give 1,3-oxazol-2-hydrazones which, without being isolated, can react with dimethylacetylene dicarboxylate to afford furo[2,3-d]pyridazin-4(5H)-ones with an unprecedented level of complexity in a triple domino Diels-Alder/retro-Diels-Alder/lactamization reaction sequence.

引用

页码：3964 / 3967

页数：4

共 42 条

[1] Asif M, 2012, CURR MED CHEM, V19, P2984
[2] Pyridazin-3(2H)-ones: the versatile pharmacophore of medicinal significance
Bansal, Ranju
Thota, Sridhar
[J]. MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (06) : 2539 - 2552
[3] Boukharsa Y., 2014, J. Chem. Pharm. Res., V6, P297, DOI [10.1002/chin.201524275, DOI 10.1002/CHIN.201524275]
[4] Annelation of perfluorinated heteroaromatic systems by 1,3-dicarbonyl derivatives
Cartwright, Matthew W.
Parks, Emma L.
Pattison, Graham
Slater, Rachel
Sandford, Graham
Wilson, Ian
Yufit, Dmitrii S.
Howard, Judith A. K.
Christopher, John A.
Miller, David D.
[J]. TETRAHEDRON, 2010, 66 (17) : 3222 - 3227
[5] Chowdary K. P. R., 2011, ASIAN J CHEM, V23, P1905
[6] 6-PHENYL-4,5-DIHYDRO-3(H-2)-PYRIDAZINONES - SERIES OF HYPOTENSIVE AGENTS
CURRAN, WV
ROSS, A
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (03) : 273 - 281
[7] Chemistry and Biology Of Multicomponent Reactions
Domling, Alexander
Wang, Wei
Wang, Kan
[J]. CHEMICAL REVIEWS, 2012, 112 (06) : 3083 - 3135
[8] Pyridazines.: XV.: Synthesis of 6-aryl-5-amino-3(2H)-pyridazinones as potential platelet aggregation inhibitors
Estevez, I
Raviña, E
Sotelo, E
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (06) : 1421 - 1428
[9] Synthesis of polysubstituted 4,5,6,7-tetrahydrofuro[2,3-c]pyridines by a novel multicomponent reaction
Fayol, A
Zhu, JP
[J]. ORGANIC LETTERS, 2004, 6 (01) : 115 - 118
[10] Fayol A, 2002, ANGEW CHEM INT EDIT, V41, P3633, DOI 10.1002/1521-3773(20021004)41:19<3633::AID-ANIE3633>3.0.CO

← 1 2 3 4 5 →