Transition metal and base free coupling of N-tosylhydrazones with 1,3-dicarbonyl compound

被引：10

作者：

Choudhary, Deepika ^{[1
]}

Agrawal, Chanchal ^{[1
]}

Khatri, Vineeta ^{[1
]}

Thakuria, Ranjit ^{[2
]}

Basak, Ashok K. ^{[1
]}

机构：

[1] Univ Rajasthan, Dept Chem, JLN Marg, Jaipur 302004, Rajasthan, India

[2] Gauhati Univ, Dept Chem, Gauhati 781014, Assam, India

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 12期

关键词：

N-Tosylhydrazone; Tetraketone; beta-Keto enol ether; Transition metal free C-O coupling; Xanthenedione; BOND FORMATION; STRAIGHTFORWARD SYNTHESIS; CARBONYL-COMPOUNDS; DIAZO-COMPOUNDS; IONIC LIQUID; ROUTE; SULFONYLHYDRAZONES; DERIVATIVES; ALKYLATION; ALDEHYDES;

D O I：

10.1016/j.tetlet.2017.02.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-tosylhydrazones derived from a wide variety of aryl, alkyl and heteroaryl aldehydes undergo smooth coupling with 5,5-dimethylcyclohexane-1,3-dione under transition metal and base free conditions to generate tetraketo compounds in high yields. In presence of a base, the coupling reaction generates beta-keto enol ether as the major product in a polar aprotic solvent. N-Tosylhydrazone can also be converted to xanthenedione in high yields in one-pot operation under mild acidic conditions. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：1132 / 1136

页数：5

共 44 条

[1] A new protocol for the in situ generation of aromatic, heteroaromatic, and unsaturated diazo compounds and its application in catalytic and asymmetric epoxidation of carbonyl compounds. Extensive studies to map out scope and limitations, and rationalization of diastereo- and enantioselectivities
Aggarwal, VK
Alonso, E
Bae, I
Hynd, G
Lydon, KM
Palmer, MJ
Patel, M
Porcelloni, M
Richardson, J
Stenson, RA
Studley, JR
Vasse, JL
Winn, CL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) : 10926 - 10940
[2] [Anonymous], 2011, ANGEW CHEM
[3] [Anonymous], 2012, ANGEW CHEM INT EDIT
[4] EFFECT OF METAL-IONS IN ORGANIC-SYNTHESIS .16. KNOEVENAGEL CONDENSATIONS OF ALDEHYDES AND TOSYLHYDRAZONES WITH 2,4-PENTANEDIONE BY COPPER (II) CHLORIDE-CATALYZED REACTION
ATTANASI, O
FILIPPONE, P
MEI, A
[J]. SYNTHETIC COMMUNICATIONS, 1983, 13 (14) : 1203 - 1208
[5] Copper Acetoacetonate [Cu(acac)2]/BINAP-Promoted Csp3-N Bond Formation via Reductive Coupling of N-Tosylhydrazones with Anilines
Aziz, Jessy
Brion, Jean-Daniel
Hamze, Abdallah
Alami, Mouad
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) : 2417 - 2429
[6] THE DECOMPOSITION OF TOLUENE-PARA-SULPHONYLHYDRAZONES BY ALKALI
BAMFORD, WR
STEVENS, TS
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1952, (DEC): : 4735 - 4740
[7] Barluenga J, 2010, ANGEW CHEM, V122, P7008
[8] Barluenga J., 2010, Angew. Chem, V122, P5113, DOI [10.1002/ange.201001704, DOI 10.1002/ANGE.201001704]
[9] Barluenga J., 2011, ANGEW CHEM, V123, P7626
[10] Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions
Barluenga, Jose
Valdes, Carlos
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) : 7486 - 7500

← 1 2 3 4 5 →