Synthesis of novel ?-butyrolactone-based phenazine compounds via microwave-assisted multicomponent domino reactions

被引:2
作者
Nguyen, Ha-Thanh [1 ,2 ]
Thi, Phuong Hoang [1 ]
Le-Nhat-Thuy, Giang [1 ,2 ]
Thi, Quynh Giang Nguyen [1 ,2 ]
Nguyen, Tuan Anh [1 ]
Thi, Tuyet Anh Dang [1 ,2 ]
Nguyen, Tuyen Van [1 ,2 ]
机构
[1] Vietnam Acad Sci & Technol, Inst Chem, 18 Hoang Quoc Viet St, Hanoi, Vietnam
[2] Vietnam Acad Sci & Technol, Grad Univ Sci & Technol, 18 Hoang Quoc Viet St, Hanoi, Vietnam
关键词
gamma-butyrolactone; naphthoquinone; phenazine; microwave-assisted multicomponent reaction; ANTITUMOR-ACTIVITY; TOPOISOMERASE-I; GREEN SYNTHESIS; DERIVATIVES; INHIBITOR; FUNGUS; ANALOGS;
D O I
10.1007/s10593-023-03152-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of new and significative gamma-butyrolactone-based phenazines were synthesized through two-step one-pot five-component reactions of 2-hydroxy-1,4-naphthoquinone, a variety of aromatic aldehydes, benzene-1,2-diamine, tetronic acid, and ammonium acetate in glacial acetic acid. The synthesis proceeded via condensation, Michael addition, tautomerization sequence of steps. All the synthesized compounds were fully characterized by spectral data.
引用
收藏
页码:749 / 755
页数:7
相关论文
共 54 条
[1]  
Abadi A. Y. E., 2017, CHIN CHEM SOC, V64, P690
[2]   An efficient four-component domino protocol for the rapid and green synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives using caffeine as a homogeneous catalyst [J].
Abadi, Afshin Yazdani Elah ;
Maghsoodlou, Malek-Taher ;
Heydari, Reza ;
Mohebat, Razieh .
RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (02) :1227-1235
[3]   New phenyl derivatives from endophytic fungus Aspergillus flavipes AIL8 derived of mangrove plant Acanthus ilicifolius [J].
Bai, Zhi-Qiang ;
Lin, Xiuping ;
Wang, Yizhu ;
Wang, Junfeng ;
Zhou, Xuefeng ;
Yang, Bin ;
Liu, Juan ;
Yang, Xianwen ;
Wang, Yi ;
Liu, Yonghong .
FITOTERAPIA, 2014, 95 :194-202
[4]   REVISED STRUCTURE FOR THE PHENAZINE ANTIBIOTIC FROM PSEUDOMONAS-FLUORESCENS 2-79 (NRRL B-15132) [J].
BRISBANE, PG ;
JANIK, LJ ;
TATE, ME ;
WARREN, RFO .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1987, 31 (12) :1967-1971
[5]   Novel phthalide derivatives: Synthesis and anti-inflammatory activity in vitro and in vivo [J].
Chen, Liu Zeng ;
Wu, Jing ;
Li, Kang ;
Wu, Qian Qian ;
Chen, Rui ;
Liu, Xin Hua ;
Ruan, Ban Feng .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 206
[6]  
Choudhary A.S., 2014, CAN CHEM T, V2, P365, DOI DOI 10.13179/CANCHEMTRANS.2014.02.04.0122
[7]   New leishmanicidal physalins from Physalis minima [J].
Choudhary, M. Iqbal ;
Yousuf, Sammer ;
Samreen ;
Ahmed, Shakil ;
Atta-Ur-Rahman .
NATURAL PRODUCT RESEARCH, 2007, 21 (10) :877-883
[8]   Sonochemical multi-component synthesis of spirooxindoles [J].
Dabiri, Minoo ;
Tisseh, Zeinab Noroozi ;
Bahramnejad, Mahboobeh ;
Bazgir, Ayoob .
ULTRASONICS SONOCHEMISTRY, 2011, 18 (05) :1153-1159
[9]   Design, Synthesis, and Cytotoxic Evaluation of Novel Lupane Triterpenoid Derived Hydroxamates [J].
Dang Thi Tuyet Anh ;
Dinh Thi Cuc ;
Le Nhat Thuy Giang ;
Nguyen Thi Hien ;
Vu Ngoc Doan ;
Nguyen Ha Thanh ;
Nguyen Van Tuyen ;
Phan Van Kiem .
NATURAL PRODUCT COMMUNICATIONS, 2020, 15 (06)
[10]   Antimalarial activity of phenazines from lapachol, β-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo [J].
de Andrade-Neto, VF ;
Goulart, MOF ;
da Silva, JF ;
da Silva, MJ ;
Pinto, MD ;
Pinto, AV ;
Zalis, MG ;
Carvalho, LH ;
Krettli, AU .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (05) :1145-1149