One-pot synthesis of 5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one derivatives

被引：10

作者：

Dong, Hong-Ru ^{[1
]}

Gao, Zhong-Lian ^{[1
]}

Li, Rong-Shan ^{[1
]}

Hu, Yi-Ming ^{[2
]}

Dong, Heng-Shan ^{[1
]}

Xie, Zhi-Xiang ^{[1
]}

机构：

[1] Lanzhou Univ, Inst Organ Chem, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China

[2] Lanzhou Univ, Sch Nucl Sci & Technol, Lanzhou 730000, Gansu, Peoples R China

来源：

RSC ADVANCES | 2014年 / 4卷 / 99期

关键词：

CARBONIC-ANHYDRASE INHIBITORS; FORMIC-ACID; ANTIMICROBIAL ACTIVITY; SELECTIVE INHIBITORS; REDUCTIVE AMINATION; SCHIFF-BASES; 2-AMINO-1,3,4-THIADIAZOLES; HETEROCYCLES; MECHANISM; AMINES;

D O I：

10.1039/c4ra02714k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel and efficient one-pot method has been developed for the synthesis of 2-substituted-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one derivative by the combination of [3 + 3] cycloaddition, reduction, deamination reactions. The fused heterocyclic compounds 2-substituted-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-ones was synthesized by the diversity-oriented catalysis. As an extension of the synthetic methodology, some 4H-pyrido[1,2-a]pyrimidin-4-one 4a-c was synthesized. The pi-pi accumulation structure of supramolecular self-assembly was discussed in the crystal.

引用

页码：55827 / 55831

页数：5

共 46 条

[1] New thiazolidinedione-5-acetic acid amide derivatives: synthesis, characterization and investigation of antimicrobial and cytotoxic properties [J].

Alegaon, Shankar G. ;

Alagawadi, Kallanagouda R. .

MEDICINAL CHEMISTRY RESEARCH, 2012, 21 (06) :816-824

[2] Synthesis and autoxidation of new tetracyclic 9H,10H-indolizino[1,2-b]indole-1-ones [J].

Bhattacharya, G ;

Su, TL ;

Chia, CM ;

Chen, KT .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) :426-432

[3] Spectroscopic evidence of a free-radical mechanism in the reduction of Schiff bases by formic acid [J].

Bianchini, R ;

Forte, C ;

Musumarra, G ;

Pinzino, C ;

Sergi, C .

TETRAHEDRON, 1997, 53 (20) :6907-6916

[4] 3,4,9,9A-TETRAHYDRO-1,4-ETHANO-3,4A-(IMINOETHANO)-4AH-CARBAZOL-2(1H)-ONE DERIVATIVES .2. UNUSUAL RESULTS FROM ESCHWEILER CLARKE METHYLATION [J].

BOBOWSKI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (07) :929-931

[5]

Busch B, 2005, Preparation of 3-phenyl-N-(1,3,4-thiadiazol-2-yl)acrylamide derivatives and related compounds as modulators of estrogen-related receptors for the treatment of diseases such as cancer, rheumatoid arthritis or neurological disorders, Patent No. [2005/072731A1, 2005072731]

[6] Carbonic anhydrase inhibitors. Part 86. A QSAR study on some sulfonamide drugs which lower intra-ocular pressure, using the ACE non-linear statistical method [J].

Clare, BW ;

Supuran, CT .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (09) :859-865

[7] Multicomponent one-pot procedure for the synthesis of free α-chiral amines from aldehydes [J].

Côté, A ;

Charette, AB .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (26) :10864-10867

[8] Synthesis of β-cyanopropan-1-one derivates by domino reaction [J].

Dong, Hong-Ru ;

Dong, Wang-Jun ;

Li, Rong-Shan ;

Hu, Yi-Ming ;

Dong, Heng-Shan ;

Xie, Zhi-Xiang .

GREEN CHEMISTRY, 2014, 16 (07) :3454-3457

[9] Virtual Screening Identification of Nonfolate Compounds, Including a CNS Drug, as Antiparasitic Agents Inhibiting Pteridine Reductase [J].

Ferrari, Stefania ;

Morandi, Federica ;

Motiejunas, Domantas ;

Nerini, Erika ;

Henrich, Stefan ;

Luciani, Rosaria ;

Venturelli, Alberto ;

Lazzari, Sandra ;

Calo, Samuele ;

Gupta, Shreedhara ;

Hannaert, Veronique ;

Michels, Paul A. M. ;

Wade, Rebecca C. ;

Costi, M. Paola .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (01) :211-221

[10] N-Heterocyclic Carbene Catalyzed Domino Reactions [J].

Grossmann, Andre ;

Enders, Dieter .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (02) :314-325

← 1 2 3 4 5 →