Ionic Liquid [PyN(CH2)(4)SO3H][CH3PhSO3] Mediated & Promoted Eco- Friendly One- Pot Domino Synthesis of Benzothiazolopyrano/Chromenopyrimidine Derivatives

被引：7

作者：

Arya, Kritika ^{[1
]}

Kumar, Sudesh ^{[1
]}

Arya, Anand Kumar ^{[2
]}

Kumar, Mahendra ^{[3
]}

机构：

[1] Banasthali Vidyapith, Dept Chem, Vanasthali 304022, Rajasthan, India

[2] Reg Inst Educ, DESM, Ajmer 305004, India

[3] Univ Rajasthan, Dept Chem, Jaipur 302018, Rajasthan, India

来源：

CURRENT ORGANOCATALYSIS | 2018年 / 5卷 / 03期

关键词：

Benzothiazolochromeno-pyrimidinones; benzothiazolopyranopyrimidinones; ionic liquid; multicomponent domino reaction;

D O I：

10.2174/2213337205666181003142757

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Background: The pyridinium based p-toluenesulfonic acid functionalized [Py(CH2)(4)SO3H][CH3PhSO3] ionic liquid has been employed as eco-friendly solvent cum promoter for the multicomponent domino heterocyclization of substituted 2-aminobenzothiazoles with 4-hydroxy-6-methyl-2-pyrone / 4-hydroxycoumarin and aryl aldehydes to produce benzothiazolo[2,3-b]pyrano [3,4-e]pyrimidin-4-ones and benzothiazole [2,3-b]chromeno[3,4-e]pyrimidin-6-one in excellent yields. Methods and results: Three-component synthesis of structurally diverse benzothiazolopyrano/ chromenopyrimidines, incorporating the privileged heterocyclic scaffolds of medicinal relevance has been carried out by the reaction of substituted 2-aminobenzothiazoles with 4-hydroxy-6-methyl-2-pyrone / 4-hydroxycoumarin and aryl aldehydes in pyridinium based p-toluenesulfonic acid functionalized ionic liquid. The Bronsted acidic ionic liquid could be reused five-times without a significant loss of catalytic activity. Conclusion: The protocol proves to be efficient and facile in terms of high yields, operational simplicity, reduced reaction time and ease of recovery of the reaction medium.

引用

页码：222 / 228

页数：7

共 43 条

[1]

Arya AK, 2014, LETT DRUG DES DISCOV, V11, P594

[2] A domino protocol for the efficient synthesis of structurally diverse benzothiazolylquinoline-2,5-diones and their spiro analogues [J].

Arya, Anand Kumar ;

Gupta, Sunil Kumar ;

Kumar, Mahendra .

TETRAHEDRON LETTERS, 2012, 53 (45) :6035-6038

[3] Base catalyzed multicomponent synthesis of spiroheterocycles with fused heterosystems [J].

Arya, Anand Kumar ;

Kumar, Mahendra .

MOLECULAR DIVERSITY, 2011, 15 (03) :781-789

[4] An efficient green chemical approach for the synthesis of structurally diverse spiroheterocycles with fused heterosystems [J].

Arya, Anand Kumar ;

Kumar, Mahendra .

GREEN CHEMISTRY, 2011, 13 (05) :1332-1338

[5] Recent developments on ultrasound-assisted one-pot multicomponent synthesis of biologically relevant heterocycles [J].

Banerjee, Bubun .

ULTRASONICS SONOCHEMISTRY, 2017, 35 :15-35

[6] Medicinal attributes of pyrazolo[3,4-d]pyrimidines: A review [J].

Chauhan, Monika ;

Kumar, Raj .

BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (18) :5657-5668

[7] Lipase-initiated one-pot synthesis of spirooxazino derivatives: redesign of multicomponent reactions to expand substrates scope and application potential [J].

Chen, Xiao-Yang ;

Wang, Jun-Liang ;

Lin, Xian-Fu ;

Wu, Qi .

TETRAHEDRON, 2016, 72 (23) :3318-3323

[8] The anti-proliferative activity of novel 4H-benzo[h] chromenes, 7H-benzo[h]-chromeno[2,3-d] pyrimidines and the structure-activity relationships of the 2-,3-positions and fused rings at the 2, 3-positions [J].

El-Agrody, Ahmed M. ;

Halawa, Ahmed H. ;

Fouda, Ahmed M. ;

Al-Dies, Al-Anood M. .

JOURNAL OF SAUDI CHEMICAL SOCIETY, 2017, 21 (01) :82-90

[9] Novel Pyrimidine Tagged Silver Nanoparticle Based Fluorescent Immunoassay for the Detection of Pseudomonas aeruginosa [J].

Ellairaja, Sundaram ;

Krithiga, Narayanaswamy ;

Ponmariappan, Sarkaraisamy ;

Vasantha, Vairathevar Sivasamy .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2017, 65 (08) :1802-1812

[10] Synthesis of some new pyrazolo[3,4-d]pyrimidine derivatives of expected anticancer and radioprotective activity [J].

Ghorab, Mostafa M. ;

Ragab, Fatma A. ;

Alqasoumi, Saleh I. ;

Alafeefy, Ahmed M. ;

Aboulmagd, Sarah A. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (01) :171-178

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