Cu-Catalyzed Synthesis of [1,2,3]triazolo[1,5-c]quinazolin-5(6H)-one Derivatives via Sequential Reaction of Ethyl-2-(2-oxoindolin-3-ylidene)acetate with Sodium Azide

被引：0

作者：

Ghosh, Somnath ^{[1
]}

Mohanta, Nirmala ^{[1
]}

Gnanaprakasam, Boopathy ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res IISER Pune, Dept Chem, Dr Homi Bhabha Rd, Pune 411008, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 30期

关键词：

Copper catalyst; Ring expansion; Heterocycle; Rearrangement; Domino reaction; ONE-POT SYNTHESIS; CLICK CHEMISTRY; TANDEM; CYCLOADDITIONS; BINDING;

D O I：

10.1002/ejoc.202400443

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report a novel and efficient method for the synthesis of new class of 5-oxo-5,6-dihydro-[1,2,3]triazolo[1,5-c]quinazoline derivatives by copper-catalyzed reaction of alpha, beta-unsaturated keto/ester methyleneindolinone with sodium azide at room temperature via an azide-alkene cyclization and ring expansion rearrangement. This method is applicable to a variety of alpha, beta-unsaturated keto/ester methyleneindolinone and displayed wide functional group tolerance.

引用

收藏

页数：5

相关论文

共 30 条

[1] Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].

Agalave, Sandip G. ;

Maujan, Suleman R. ;

Pore, Vandana S. .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718

[2] SYNTHESIS AND ORAL ANTIALLERGIC ACTIVITY OF CARBOXYLIC-ACIDS DERIVED FROM IMIDAZO[2,1-C][1,4]BENZOXAZINES, IMIDAZO[1,2-A]QUINOLINES, IMIDAZO[1,2-A]QUINOXALINES, IMIDAZO[1,2-A]QUINOXALINONES, PYRROLO[1,2-A]QUINOXALINONES, PYRROLO[2,3-A]QUINOXALINONES, AND IMIDAZO[2,1-B]BENZOTHIAZOLES [J].

AGER, IR ;

BARNES, AC ;

DANSWAN, GW ;

HAIRSINE, PW ;

KAY, DP ;

KENNEWELL, PD ;

MATHARU, SS ;

MILLER, P ;

ROBSON, P ;

ROWLANDS, DA ;

TULLY, WR ;

WESTWOOD, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (06) :1098-1115

[3] Recent advances in the pharmacological diversification of quinazoline/quinazolinone hybrids [J].

Auti, Prashant S. ;

George, Ginson ;

Paul, Atish T. .

RSC ADVANCES, 2020, 10 (68) :41353-41392

[4] New 1,2,3-triazolo[1,5-a]quinoxalines: synthesis and binding to benzodiazepine and adenosine receptors. II [J].

Biagi, G ;

Giorgi, I ;

Livi, O ;

Scartoni, V ;

Betti, L ;

Giannacini, G ;

Trincavelli, ML .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2002, 37 (07) :565-571

[5] Chemoselective Reduction of Isatin-Derived Electron-Deficient Alkenes Using Alkylphosphanes as Reduction Reagents [J].

Cao, Shu-Hua ;

Zhang, Xiu-Chun ;

Wei, Yin ;

Shi, Min .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (14) :2668-2672

[6] Synthesis, ionotropic glutamate receptor binding affinity, and structure-activity relationships of a new set of 4,5-dihydro-8-heteroaryl-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates analogues of TQX-173 [J].

Catarzi, D ;

Colotta, V ;

Varano, F ;

Filacchioni, G ;

Galli, A ;

Costagli, C ;

Carlà, V .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (19) :3157-3165

[7] Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals [J].

Climent, Maria J. ;

Corma, Avelino ;

Iborra, Sara .

CHEMICAL REVIEWS, 2011, 111 (02) :1072-1133

[8] A Survey of the Structures of US FDA Approved Combination Drugs [J].

Das, Pradipta ;

Delost, Michael D. ;

Qureshi, Munaum H. ;

Smith, David T. ;

Njardarson, Jon T. .

JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (09) :4265-4311

[9] INTRAMOLECULAR [4+2] CYCLO-ADDITIONS OF NITROSOALKENES WITH OLEFINS [J].

DENMARK, SE ;

DAPPEN, MS ;

STERNBERG, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (24) :4741-4743

[10] Tandem [4+2]/[3+2] cycloadditions of nitroalkenes [J].

Denmark, SE ;

Thorarensen, A .

CHEMICAL REVIEWS, 1996, 96 (01) :137-165