Novel Annulation of Cyanuric Chloride with 2-Aminobenzamides: A New Approach to 2-Amino-3-substituted Quinazolin-4(3H)-ones

被引：9

作者：

Soda, Anil Kumar ^{[1
,2
]}

Sriramoju, Vinodkumar ^{[1
]}

Chellu, Ramesh Kumar ^{[1
,2
]}

Chilaka, Sai Krishna ^{[1
,2
]}

Kurva, Srinivas ^{[1
]}

Bansod, Sudhakar ^{[1
,2
]}

Madabhushi, Sridhar ^{[1
,2
]}

机构：

[1] CSIR, Fluoroagro Chem Dept, Indian Inst Chem Technol, Hyderabad 500007, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

来源：

CHEMISTRYSELECT | 2021年 / 6卷 / 04期

关键词：

2-Amino N-substituted benzamide; Annulation; Cyanuric Chloride; Metal-free reaction; ONE-POT SYNTHESIS; THYMIDYLATE SYNTHASE; REGIOSELECTIVE SYNTHESIS; INHIBITORS; 2-AMINOQUINAZOLIN-4(3H)-ONE; ORGANOCATALYST; DISCOVERY; ROUTE; ACIDS; MILD;

D O I：

10.1002/slct.202004540

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and efficient method for preparation of 2-amino- 3-substituted quinazolin-4(3H)-ones by reaction of cyanuric chloride with 2-amino N-substituted benzamides in acetonitrile-water (2 : 1) using sodium bicarbonate as a mild base is described. Using this metal-free method, a variety of 2-amino-3-substituted quinazolin-4(3H)-ones were obtained in good to excellent yields. Here, both organic and inorganic bases were found to promote this reaction and the best results were observed with sodium bicarbonate. This study is the first observation of cyanuric chloride to act as a source for creation of amine functionality in 2-amino-3-substituted quinazolin-4(3H)-ones.

引用

页码：896 / 901

页数：6

共 50 条

[21] An efficient HCCP-mediated direct amination of quinazolin-4(3H)-ones
Shen, Zhenlu
He, Xiaofei
Dai, Jialiang
Mo, Weimin
Hu, Baoxiang
Sun, Nan
Hu, Xinquan
TETRAHEDRON, 2011, 67 (09) : 1665 - 1672
[22] Synthesis and Antineoplastic Properties of 3-Substituted 5,5-Dimethylbenzo[h]Quinazolin-4(3H)-Ones
Markosyan, A. I.
Torshirzad, N. M.
Shakhbazyan, G. H.
Arsenyan, F. G.
PHARMACEUTICAL CHEMISTRY JOURNAL, 2014, 47 (12) : 651 - 654
[23] Copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-ones from benzyl-substituted anthranilamides
Foroumadi, Parham
Lotfi, Vahid
Mahdavi, Mohammad
Moghimi, Setareh
Soheiliza, Mehdi
Kianmehr, Ebrahim
Firoozpour, Loghman
Asadipour, Alj
Foroumadi, Alireza
HETEROCYCLIC COMMUNICATIONS, 2018, 24 (05) : 267 - 271
[24] The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX
Alam, Md Toufique
Maiti, Saikat
Mal, Prasenjit
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 2396 - 2403
[25] Vibrational spectra and computational study of 3-amino-2-phenyl quinazolin-4(3H)-one
Panicker, C. Yohannan
Varghese, Hema Tresa
Ambujakshan, K. R.
Mathew, Samuel
Ganguli, Subarna
Nanda, Ashis Kumar
Van Alsenoy, Christian
Mary, Y. Sheena
JOURNAL OF MOLECULAR STRUCTURE, 2010, 963 (2-3) : 137 - 144
[26] KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes
Nomula, Vishnuvardhan
Rao, Sadu Nageswara
SYNTHETIC COMMUNICATIONS, 2021, 51 (17) : 2602 - 2612
[27] Regioselective Sulfonylation and N- to O-Sulfonyl Migration of Quinazolin-4(3H)-ones and Analogous Thienopyrimidin-4(3H)-ones
Mertens, Matthias D.
Pietsch, Markus
Schnakenburg, Gregor
Guetschow, Michael
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18) : 8966 - 8979
[28] FeCl3-Mediated Synthesis of 2-(Trifluoromethyl)quinazolin-4(3H)-ones from Isatins and Trifluoroacetimidoyl Chlorides
Wang, Le-Cheng
Du, Shiying
Chen, Zhengkai
Wu, Xiao-Feng
ORGANIC LETTERS, 2020, 22 (14) : 5567 - 5571
[29] Synthesis of 2, 3-Disubstituted-Quinazolin-4-(3H)-ones
Patil, D. A.
Patil, P. O.
Patil, G. B.
Surana, S. J.
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2011, 11 (08) : 633 - 641
[30] Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones
Li, Ting
Chen, Minglu
Yang, Lei
Xiang, Zhengxin
Wang, Yongwei
Li, Fei
Chen, Dongyin
TETRAHEDRON, 2016, 72 (06) : 868 - 874

← 1 2 3 4 5 →