An efficient Bronsted acid ionic liquid catalyzed synthesis of novel spiro1,2,4-triazolidine-5-thiones and their photoluminescence study

被引：9

作者：

Shinde, Vikas B. ^{[1
]}

Mhaldar, Pradeep M. ^{[1
]}

Chhowala, Tarulata N. ^{[2
]}

Mirzaei, Mahmoud ^{[3
]}

Ghotekar, Suresh K. ^{[4
]}

Rashinkar, Gajanan S. ^{[1
]}

Pore, Dattaprasad M. ^{[1
]}

机构：

[1] Shivaji Univ, Dept Chem, Kolhapur 416004, Maharashtra, India

[2] Veer Narmad South Gujarat Univ, Dept Chem, Surat 395007, India

[3] Isfahan Univ Med Sci, Res Inst Primordial Prevent Noncommunicable Dis, Esfahan, Iran

[4] Univ Mumbai, Smt Devkiba Mohansinhji Chauhan Coll Commerce & S, Dept Chem, Dadra Nagar Haveli 396230, UT, India

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2022年 / 1249卷

关键词：

11H-Indeno[1,2-b]quinoxalin-2-one; Thiosemicarbazide; Ionic liquid; Spiro 1,2,4-triazolidine-5-thione; Bronsted acid; ONE-POT; MULTICOMPONENT SYNTHESIS; IN-VITRO; DESIGN; DISSOCIATION; ACETONITRILE; DERIVATIVES; ANTICANCER; TRIAZOLES; ACCESS;

D O I：

10.1016/j.molstruc.2021.131528

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：

We have synthesized a novel Bronsted acidic ionic liquid, 1-(2-hydroxyethyl)-1-(4-sulfobutyl)piperidin1-ium hydrogen sulfate, [HEPiPYBSA](+) HSO4- and explored its catalytic efficiency for synthesis of indenoquinoxalone tethered spiro-1,2,4-triazolidine-5-thiones from reaction of 11H-[1,2-b]quinoxalin-11-one and thiosemicarbazide. The most stable geometries of synthesized ionic liquid (IL) [HEPiPYBSA](+) HSO4- were obtained through systematically optimization by the DFT theory at B3LYP/6-31G* level. A photoluminescence study of the synthesized spiro-1,2,4-triazolidine-5-thiones revealed a remarkable fluorescent activity. The advantages of the present method are a reusable hydrophilic green catalyst, mild reaction conditions, use of benign solvent system, short reaction span, high atom economy and wide substrate scope. (C) 2021 Elsevier B.V. All rights reserved.

引用

页数：11

共 50 条

[1] An efficient Brønsted acid ionic liquid catalyzed synthesis of novel spiro1,2,4-triazolidine-5-thiones and their photoluminescence study
Shinde, Vikas B.
Mhaldar, Pradeep M.
Chhowala, Tarulata N.
Mirzaei, Mahmoud
Ghotekar, Suresh K.
Rashinkar, Gajanan S.
Pore, Dattaprasad M.
Journal of Molecular Structure, 2022, 1249
[2] SYNTHESIS OF 1-PHENYL-3,3-DIALKYL-1,2,4-TRIAZOLIDINE-5-THIONES
SCHILDKNECHT, H
RENNER, G
ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1972, 761 (JUL): : 189 - +
[3] Novel task-specific ionic liquid for room temperature synthesis of spiro-1,2,4-triazolidine-3-thiones
Suyog N. Korade
Jayavant D. Patil
Dattaprasad M. Pore
Monatshefte für Chemie - Chemical Monthly, 2016, 147 : 2143 - 2149
[4] Novel task-specific ionic liquid for room temperature synthesis of spiro-1,2,4-triazolidine-3-thiones
Korade, Suyog N.
Patil, Jayavant D.
Pore, Dattaprasad M.
MONATSHEFTE FUR CHEMIE, 2016, 147 (12): : 2143 - 2149
[5] SYNTHESIS OF HETEROCYCLIC-COMPOUNDS FROM "3-SILA-1,2,4-TRIAZOLIDINE-5-THIONES
BUCHWALD, H
RUHLMANN, K
ZEITSCHRIFT FUR CHEMIE, 1978, 18 (09): : 336 - 337
[6] L-Proline Nitrate: An Efficient Amino Acid Ionic Liquid Catalyzed Synthesis of 5-aryl-[1,2,4]-triazolidine-3-thiones
Sonawane, Suraj A.
Pore, Dattaprasad M.
LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (09) : 743 - 749
[7] [C16MPy]AlCl3Br: an efficient novel ionic liquid for synthesis of novel 1,2,4-triazolidine-3-thiones in water
Patil, Jayavant D.
Pore, Dattaprasad M.
RSC ADVANCES, 2014, 4 (28) : 14314 - 14319
[8] A Mechanistic Approach to Liquid-Assisted Mechanochemical Synthesis of 5-Aryl/Spiro-[1,2,4]-triazolidine-3-thiones
Dutta, Anurag
Saikia, Raktim Abha
Thakur, Ashim Jyoti
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (34)
[9] Novel, green and sustainable route for synthesis of 5-aryl-4-phenyl-1,2,4-triazolidine-3-thiones
Patil, Mayuri
Mhaldar, Pradeep
Mahadik, Vrushali
Pore, Dattaprasad M.
TETRAHEDRON LETTERS, 2020, 61 (25)
[10] Waste to wealth: agro-waste catalyzed green method synthesis of 5-aryl-1,2,4-triazolidine-3-thiones and 1,2,4-triazospiro-3-thiones
Khatavi, Santosh Y.
Kantharaju, Kamanna
ORGANIC COMMUNICATIONS, 2021, 14 (03) : 240 - 254

← 1 2 3 4 5 →