Microwave-Assisted Rapid Synthesis of Pyrido[2,3-d:6,5-d]dipyrimidine-2,4,6,8-tetraones over Sulfonic Acid Functionalized Imidazolium Salts under Solvent-Free Condition

被引:10
作者
Saikia, Lakhinath [1 ,3 ]
Namsa, Nima. D. [2 ]
Thakur, A. J. [3 ]
机构
[1] Rajiv Gandhi Univ, Dept Chem, Rono Hills, Doimukh 791112, Arunachal Prade, India
[2] Tezpur Univ, Dept Mol Biol & Biotechnol, Napaam 784028, Assam, India
[3] Tezpur Univ, Dept Chem Sci, Napaam 784028, Assam, India
关键词
Dsim]Cl; Ionic liquids; Microwave chemistry; Pyrido[2,3-d:6,5-d]dipyrimidine; Solvent-free; PRELIMINARY ANTIBACTERIAL PROPERTIES; IONIC LIQUIDS; EFFICIENT SYNTHESIS; ONE-POT; DERIVATIVES; CATALYST; IRRADIATION; INHIBITORS; QUINAZOLINE; ALPHA;
D O I
10.1002/slct.201701384
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Seven numbers of sulfonic acid functionalized imidazolium salts (ionic liquids) have been tested for the synthesis of pyrido[2,3-d:6,5-d]dipyrimidine-2,4,6,8-tetrone derivative with completely aromatic pyridine ring. [Dsim]Cl is found to be the best among them to carry out the synthesis via condensation of 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione with aromatic aldehydes within minutes under microwave irradiation, paving the way for an excellent methodology towards the synthesis of a series of pyrido[2,3-d:6,5-d]dipyrimidine-2,4,6,8-tetrone. The catalyst can easily be recovered and reproduced, and the reproduced catalyst is found to be equally effective as the fresh one for the purpose. The methodology is quite simple, fast and general. In comparison to already described methodologies, it enjoys additional advantage of being carried out under solvent-free condition. The synthesized compounds are found to possess remarkable activity against S. aureus and K. pneumonia among the tested bacterial strains.
引用
收藏
页码:7553 / 7557
页数:5
相关论文
共 33 条
[1]   Efficient synthesis of thiazoloquinazolinone derivatives [J].
Alexandre, FR ;
Berecibar, A ;
Wrigglesworth, R ;
Besson, T .
TETRAHEDRON LETTERS, 2003, 44 (24) :4455-4458
[2]   One-pot synthesis of annulated pyrido[2,3-d:6,5-d]dipyrimidine derivatives using nitrogen based DBU catalyst in aqueous ethanol medium [J].
Bhat, Ajmal R. ;
Dongre, Rajendra S. .
JOURNAL OF THE TAIWAN INSTITUTE OF CHEMICAL ENGINEERS, 2015, 56 :191-195
[3]   A novel and efficient synthesis of pyrimido[4,5-d]pyrimidine-2,4,7-trione and pyrido[2,3-d:6,5-d] dipyrimidine-2,4,6,8-tetrone derivatives [J].
Dabiri, Minoo ;
Arvin-Nezhad, Harnid ;
Khavasi, Hamid Reza ;
Bazgir, Ayoob .
TETRAHEDRON, 2007, 63 (08) :1770-1774
[4]   Organic Reactions in "Green Surfactant": An Avenue to Bisuracil Derivative [J].
Das, Subrata ;
Kalita, Subarna J. ;
Bharali, Pranjal ;
Konwar, Bolin K. ;
Das, Babulal ;
Thakur, Ashim J. .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (12) :1530-1536
[5]   An efficient stereo-controlled synthesis of bis-pyrimido-[4,5-d]-pyrimidine derivatives via aza-Diels-Alder methodology and their preliminary bioactivity [J].
Das, Subrata ;
Thakur, Ashim Jyoti ;
Medhi, Tapas ;
Das, Babulal .
RSC ADVANCES, 2013, 3 (10) :3407-3413
[6]   A Clean, Highly Efficient and One-Pot Green Synthesis of Aryl/Alkyl/Heteroaryl-Substituted Bis(6-amino-1,3-dimethyluracil-5-yl)methanes in Water [J].
Das, Subrata ;
Thakur, Ashim Jyoti .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (12) :2301-2308
[7]   A Sustainable Multicomponent Pyrimidine Synthesis [J].
Deibl, Nicklas ;
Ament, Kevin ;
Kempe, Rhett .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (40) :12804-12807
[8]   SYNTHESIS OF 1,3,7,9-TETRAMETHYL-2,4,6,8-TETRAOXO-1,2,3,4,6,7,8,9-OCTAHYDROPYRIDO[2,3-D - 6,5-D']-DIPYRIMIINE FROM 6-AMINO-1,3-DIMETHYLURACIL AND DIMETHYL SULFOXIDE [J].
ELDERFIELD, RC ;
WHARMBY, M .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (05) :1638-+
[9]   BrOnsted Acidic Ionic Liquid as an Efficient and Reusable Catalyst for One-Pot, Three-Component Synthesis of Pyrimidinone Derivatives via Biginelli-Type Reaction Under Solvent-Free Conditions [J].
Hajipour, Abdol R. ;
Ghayeb, Yosof ;
Sheikhan, Nafisehsadat ;
Ruoho, Arnold E. .
SYNTHETIC COMMUNICATIONS, 2011, 41 (15) :2226-2233
[10]   PYRIMIDINES .52. SYNTHESIS OF PYRIDO[2,3-D]PYRIMIDINE-2,4-DIONES AND PYRIDO[2,3-D-6,5-D']DIPYRIMIDINE-2,4,6,8-TETRONES [J].
HIROTA, K ;
KITADE, Y ;
SENDA, S .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (02) :345-347