Multi-Component Reaction of 6-Aminouracils, Aldehydes and Secondary Amines: Conversion of the Products into Pyrimido[4,5-d]pyrimidines through C-H Amination/Cyclization

被引：16

作者：

Borpatra, Paran J. ^{[1
]}

Rastogi, Gaurav K. ^{[1
,2
]}

Saikia, B-S ^{[1
]}

Deb, Mohit L. ^{[1
]}

Baruah, Pranjal K. ^{[1
]}

机构：

[1] Gauhati Univ, Dept Appl Sci, GUIST, Gauhati 781014, Assam, India

[2] CSIR NEIST, Appl Organ Chem, Jorhat 785006, Assam, India

来源：

CHEMISTRYSELECT | 2019年 / 4卷 / 12期

关键词：

6-Aminouracil; 3-Component; Domino aza-Michael; C-H amination; I-2; catalyst; Pyrimidopyrimidines; ONE-POT SYNTHESIS; N-ARYL-TETRAHYDROISOQUINOLINES; OXIDATIVE COUPLING REACTIONS; BOND FUNCTIONALIZATION; GREEN SYNTHESIS; 3-COMPONENT SYNTHESIS; EFFICIENT SYNTHESIS; TERTIARY-AMINES; NITROGEN ATOM; AMINATION;

D O I：

10.1002/slct.201900210

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of 6-aminouracils with aldehydes and secondary amines catalyzed by acetic acid is reported here. This is in fact a domino aza-Michael reaction. 6-Aminouracil reacts first with aldehyde and then amine attacks the newly formed C=C bond, which is established from the mass spectral analysis of the reaction mixture. The products of the reaction are cyclized to pyrimido[4,5-d]-pyrimidines via intramolecular alpha-C-H functionalization of tertiary amine promoted by I-2-TBHP at room temperature in ethanol solvent. I-2 (10 mol %) and TBHP (1.5 eq.) are used for the cyclization reactions. Based on few controlled experiments a tentative radical mechanism is proposed for the cyclization step.

引用

页码：3381 / 3386

页数：6

共 103 条

[1] Green Chemistry: Principles and Practice [J].

Anastas, Paul ;

Eghbali, Nicolas .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312

[2]

Andivelu I, 2014, J ORG CHEM, V79, P4984

[3]

[Anonymous], 1850, LIEBIGS ANN CHEM, DOI [10.1002/jlac.18500750103, DOI 10.1002/JLAC.18500750103]

[4] An efficient one-pot three-component synthesis of pyrimido[4,5-d]pyrimidine derivatives in aqueous medium [J].

Badvel, Sreedhar ;

Gopireddy, Raveendra Reddy ;

Shaik, Thaslim Basha ;

Hasti, Sudhamani ;

Tummaluru, Veera Reddy ;

Chamarthi, Naga Raju .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (08) :749-753

[5] Formation of Aryl-bis (6-Amino-1,3-Dimethyluracil-5-yl) Methanes by reaction of 6-Amino-1, 3-Dimethyluracil with Aromatic Aldehydes [J].

Bansal, Ranju ;

Kumar, R. Sunil ;

Kumar, Gulshan ;

Thota, Sridhar ;

Thamotharan, S. ;

Parthasarathi, V. ;

Linden, Anthony .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (06) :1789-1795

[6] Copper-catalyzed oxidative sp3 C-H bond arylation with aryl boronic acids [J].

Basle, Olivier ;

Li, Chao-Jun .

ORGANIC LETTERS, 2008, 10 (17) :3661-3663

[7]

Bazgir A, 2013, IRAN J CATAL, V3, P21

[8] Ceric ammonium nitrate (CAN): an efficient and eco-friendly catalyst for the one-pot synthesis of alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methanes at room temperature [J].

Brahmachari, Goutam ;

Banerjee, Bubun .

RSC ADVANCES, 2015, 5 (49) :39263-39269

[9] The direct α-C(sp3)-H functionalisation of N-aryl tetrahydroisoquinolines via an iron-catalysed aerobic nitro-Mannich reaction and continuous flow processing [J].

Brzozowski, Martin ;

Forni, Jose A. ;

Savage, G. Paul ;

Polyzos, Anastasios .

CHEMICAL COMMUNICATIONS, 2015, 51 (02) :334-337

[10] Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity [J].

Chen, Xiao-Hua ;

Wei, Qiang ;

Luo, Shi-Wei ;

Xiao, Han ;

Gong, Liu-Zhu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) :13819-13825

← 1 2 3 4 5 6 7 8 9 10 →