Facile Non-Transition Metal-Catalyzed Synthesis of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-one Derivatives via One-Pot Multicomponent Reactions

被引:10
作者
Bahadorikhalili, Saeed [1 ]
Rahimzadeh, Golnaz [2 ]
Kianmehr, Ebrahim [2 ]
Ansari, Samira [3 ]
Hamedifar, Haleh [3 ]
Mahdavi, Mohammad [4 ]
机构
[1] Iranian Space Res Ctr, Inst Mech, Shiraz, Iran
[2] Univ Tehran, Coll Sci, Sch Chem, POB 14155-6455, Tehran, Iran
[3] Alborz Univ Med Sci, CinnaGen Med Biotechnol Res Ctr, Karaj, Iran
[4] Univ Tehran Med Sci, Endocrinol & Metab Res Ctr, Endocrinol & Metab Clin Sci Inst, Tehran 14176, Iran
关键词
dichlorocarbene; multicomponent reaction; non-metal catalysis; quinazolinone; sulfur; MAGNETIC FE3O4 NANOPARTICLES; EFFICIENT CATALYST; ISATOIC ANHYDRIDE; DESIGN; QUINAZOLINONES; AGENTS; 2-THIOXOQUINAZOLINONE; INHIBITORS; ALCOHOLS; AID;
D O I
10.1002/slct.201802861
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this paper, a novel method is introduced for the synthesis of 3-substituted 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives. This methodology is based on the multicomponent one-pot reaction of isatoic anhydride, amines, chloroform and sulfur in basic conditions. The products are obtained in highest efficiency when the reaction is performed in 1,4-dioxane as the solvent in the presence of potassium tert-butoxide as the base. The reaction showes to be efficient and simple for the preparation of these compounds. In addition, this method is general and different aromatic or aliphatic amines are used and the desired products are isolated in high yields. A possible mechanism for the reaction is proposed, which consisted the dichlorocarbene formation under the basic conditions.
引用
收藏
页码:100 / 104
页数:5
相关论文
共 47 条
[1]   Design, synthesis of 2,3-disubstitued 4(3H)-quinazolinone derivatives as anti-inflammatory and analgesic agents: COX-1/2 inhibitory activities and molecular docking studies [J].
Abdel-Aziz, Alaa A. -M. ;
Abou-Zeid, Laila A. ;
ElTahir, Kamal Eldin H. ;
Mohamed, Menshawy A. ;
Abu El-Enin, Mohamed A. ;
El-Azab, Adel S. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (16) :3818-3828
[2]   A novel method for the synthesis of 4(3H)-quinazolinones [J].
Abdel-Jalil, RJ ;
Voelter, W ;
Saeed, M .
TETRAHEDRON LETTERS, 2004, 45 (17) :3475-3476
[3]   Design, synthesis and biological evaluation of 2-mercapto-3-phenethylquinazoline bearing anilide fragments as potential antitumor agents: Molecular docking study [J].
Al-Suwaidan, Ibrahim A. ;
Alanazi, Amer M. ;
Abdel-Aziz, Alaa A. -M. ;
Mohamed, Menshawy A. ;
El-Azab, Adel S. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (13) :3935-3941
[4]   Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones [J].
Alagarsamy, Veerachamy ;
Pathak, Urvishbhai S. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (10) :3457-3462
[5]   Synthesis of 3-(aryl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives using heteropolyacids as green, heterogeneous and recyclable catalysts [J].
Allameh, S. ;
Heravi, M. M. ;
Hashemi, M. M. ;
Bamoharram, F. F. .
CHINESE CHEMICAL LETTERS, 2011, 22 (02) :131-134
[6]   Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives [J].
Asadi, Mehdi ;
Masoomi, Shiva ;
Ebrahimi, Seyed Mostafa ;
Mahdavi, Mohammad ;
Saeedi, Mina ;
Shafiee, Abbas ;
Foroumadi, Alireza .
MONATSHEFTE FUR CHEMIE, 2014, 145 (03) :497-504
[7]   Discovery of a Novel 5-HT3 Antagonist/5-HT1A Agonist 3-Amino-5,6,7,8-tetrahydro-2-{4-[4-(quinolin-2-yl)piperazin-1-yl]butyl}quinazolin-4(3H)-one (TZB-30878) as an Orally Bioavailable Agent for Irritable Bowel Syndrome [J].
Asagarasu, Akira ;
Matsui, Teruaki ;
Hayashi, Hiroyuki ;
Tamaoki, Satoru ;
Yamauchi, Yukinao ;
Minato, Kouichi ;
Sato, Michitaka .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (21) :7549-7563
[8]   An efficient one-pot procedure for preparation of 2,4(1H,3H)-qninazolinediones and 2-thioxoquinazolinone derivatives under microwave irradiation [J].
Azizian, J ;
Mohammadi, AA ;
Karimi, AR .
SYNTHETIC COMMUNICATIONS, 2003, 33 (03) :415-420
[9]   Copper supported β-cyclodextrin functionalized PEGylated mesoporous silica nanoparticle-graphene oxide hybrid: An efficient and recyclable nano-catalyst for straightforward synthesis of 2-arylbenzimidazoles and 1,2,3-triazoles [J].
Bahadorikhalili, Saeed ;
Ma'mani, Leila ;
Mahdavi, Hossein ;
Shafiee, Abbas .
MICROPOROUS AND MESOPOROUS MATERIALS, 2018, 262 :207-216
[10]   Palladium functionalized phosphinite polyethyleneimine grafted magnetic silica nanoparticles as an efficient catalyst for the synthesis of isoquinolino[1,2-b]quinazolin-8-ones [J].
Bahadorikhalili, Saeed ;
Mahdavi, Mohammad ;
Ma'mani, Leila ;
Shafiee, Abbas ;
Mahdavi, Hossein ;
Akbarzadeh, Tahmineh .
NEW JOURNAL OF CHEMISTRY, 2018, 42 (07) :5499-5507