An efficient Sn(II)-catalyzed one-pot synthesis of a 3-substituted azetidine-2,4-dione framework

被引：9

作者：

Chavan, Santosh S. ^{[1
]}

Supekar, Mrudul V. ^{[1
]}

Burate, Pralhad A. ^{[1
]}

Rupanwar, Bapurao D. ^{[1
]}

Shelke, Anil M. ^{[1
]}

Suryavanshi, Gurunath ^{[1
]}

机构：

[1] CSIR Natl Chem Lab, Chem Engn & Proc Dev Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 11期

关键词：

CATALYZED INTRAMOLECULAR AMINATION; BETA-LACTAMS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; 2,4-DISUBSTITUTED AZETIDINES; CHIRAL CATALYSTS; AMINO-ALCOHOLS; ALPHA-AMINO; ACIDS; CYCLOADDITION;

D O I：

10.1039/c7ob00294g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel Sn(II)-catalyzed tandem cyclization reaction of aromatic aldehydes with ethyl cyanoacetate has been achieved to afford a series of 3-substituted azetidine-2,4-diones in good to excellent yields. This protocol provides straightforward access to construct the azetidine core through sequential Knoevenagel condensation, hydration and the C-N cyclization reaction.

引用

收藏

页码：2385 / 2391

页数：7

相关论文

共 59 条

[1] An efficient asymmetric synthesis of azetidine 2-phosphonic acids [J].

Agami, C ;

Couty, F ;

Rabasso, N .

TETRAHEDRON LETTERS, 2002, 43 (26) :4633-4636

[2] Discovery of a Potent and Orally Efficacious TGR5 Receptor Agonist [J].

Agarwal, Sameer ;

Patil, Amit ;

Aware, Umesh ;

Deshmukh, Prashant ;

Darji, Brijesh ;

Sasane, Santosh ;

Sairam, Kalapatapu V. V. M. ;

Priyadarsiny, Priyanka ;

Giri, Poonam ;

Patel, Harilal ;

Giri, Suresh ;

Jain, Mukul ;

Desai, Ranjit C. .

ACS MEDICINAL CHEMISTRY LETTERS, 2016, 7 (01) :51-55

[3] Cu(I)-catalyzed enantioselective [2+2] cycloaddition of 1-methoxyallenylsilane with α-imino ester:: Chiral synthesis of α,β-unsaturated acylsilanes [J].

Akiyama, T ;

Daidouji, K ;

Fuchibe, K .

ORGANIC LETTERS, 2003, 5 (20) :3691-3693

[4] One-pot synthesis of arylsulfonamides and azetidine-2,4-diones via multicomponent reaction of an amine, an acetylenic compound, and an arylsuffonyl isocyanate [J].

Alizadeh, Abdolali ;

Rezvanian, Atieh .

SYNTHESIS-STUTTGART, 2008, (11) :1747-1752

[5] SYNTHESIS OF 4-THIOXO-2-AZETIDINONES [J].

BACHI, MD ;

GOLDBERG, O ;

GROSS, A ;

VAYA, J .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (08) :1477-1481

[6] Novel syntheses of azetidines and azetidinones [J].

Brandi, Alberto ;

Cicchi, Stefano ;

Cordero, Franca M. .

CHEMICAL REVIEWS, 2008, 108 (09) :3988-4035

[7] Azetidinic amino acids:: stereocontrolled synthesis and pharmacological characterization as ligands for glutamate receptors and transporters [J].

Bräuner-Osborne, H ;

Bunch, L ;

Chopin, N ;

Couty, F ;

Evano, G ;

Jensen, AA ;

Kusk, M ;

Nielsen, B ;

Rabasso, N .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (21) :3926-3936

[8] Asymmetric synthesis of α,β-diamino acid derivatives with an aziridine-, azetidine- and γ-lactone-skeleton via Mannich-type additions across α-chloro-N-sulfinylimines [J].

Callebaut, Gert ;

Mangelinckx, Sven ;

Kiss, Lorand ;

Sillanpaa, Reijo ;

Fueloep, Ferenc ;

De Kimpe, Norbert .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (11) :2326-2338

[9]

Carlin-Sinclair A, 2003, SYNLETT, P726

[10] Solvent free one-pot multi-component synthesis of β-azaarene substituted ketones via a Sn-catalyzed C(sp3)-H functionalization of 2-alkylazaarenes [J].

Chavan, Santosh S. ;

Pathan, Mohsinkhan Y. ;

Mulla, Shafeek A. R. .

RSC ADVANCES, 2015, 5 (125) :103091-103094

← 1 2 3 4 5 6 →