One-Pot Three-Component Synthesis of 4(3H)-Quinazolinones from Benzyl Halides, Isatoic Anhydride, and Primary Amines

被引:50
作者
Adib, Mehdi [1 ]
Sheikhi, Ehsan [1 ]
Bijanzadeh, Hamid Reza [2 ]
机构
[1] Univ Tehran, Univ Coll Sci, Sch Chem, Tehran, Iran
[2] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
关键词
benzyl halides; Kornblum oxidation; isatoic anhydride; amines; 4(3H)-quinazolinones; multicomponent reactions; MULTICOMPONENT REACTIONS; FACILE SYNTHESIS; MICROWAVE IRRADIATION; ASYMMETRIC-SYNTHESIS; SELECTIVE METHOD; ALKYL-HALIDES; DERIVATIVES; EFFICIENT; QUINAZOLIN-4(3H)-ONES; OXIDATION;
D O I
10.1055/s-0031-1290098
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel, one-pot, and three-component synthesis of 4(3H)-quinazolinones is described. Benzyl halides are oxidized to aldehydes under mild Kornblum conditions then undergo a three-component reaction with isatoic anhydride and primary amines to produce 4(3H)-quinazolinones in excellent yields.
引用
收藏
页码:85 / 88
页数:4
相关论文
共 57 条
[11]   A novel, one-pot, solvent-, and catalyst-free synthesis of 2-aryl/alkyl-4(3H)-quinazolinones [J].
Adib, Mehdi ;
Ansari, Samira ;
Mohammadi, Ali ;
Bijanzadeh, Hamid Reza .
TETRAHEDRON LETTERS, 2010, 51 (01) :30-32
[12]   A One-Pot, Four-Component Synthesis of N-Substituted 2,4-Diarylimidazoles [J].
Adib, Mehdi ;
Ansari, Samira ;
Feizi, Shahzad ;
Damavandi, Jafar Asgarian ;
Mirzaei, Peiman .
SYNLETT, 2009, (20) :3263-3266
[13]   Reaction between N-Isocyaniminotriphenylphosphorane, Aldehydes, and Carboxylic Acids: A One-Pot and Three-Component Synthesis of 2-Aryl-5-hydroxyalkyl-1,3,4-oxadiazoles [J].
Adib, Mehdi ;
Kesheh, Mahdi Riazati ;
Ansari, Samira ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2009, (10) :1575-1578
[14]  
[Anonymous], 2008, Comprehensive Heterocyclic Chemistry III
[15]  
Armarego W.L.F., 1967, FUSED PYRIMIDINES 1
[16]   A novel highly selective chiral auxiliary for the asymmetric synthesis of L- and D-α-amino acid derivatives via a multicomponent Ugi reaction [J].
Basso, A ;
Banfi, L ;
Riva, R ;
Guanti, G .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :575-579
[17]   One pot synthesis of 4(3H)-quinazolinones [J].
Bhat, BA ;
Sahu, DP .
SYNTHETIC COMMUNICATIONS, 2004, 34 (12) :2169-2176
[18]   Developments in furan syntheses [J].
Brown, RCD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (06) :850-852
[19]   Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains [J].
Cao, SL ;
Feng, YP ;
Jiang, YY ;
Liu, SY ;
Ding, GY ;
Li, RT .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (07) :1915-1917
[20]   Heterocycles derived from heteroatom-substituted carbenes [J].
Cheng, Y ;
Meth-Cohn, O .
CHEMICAL REVIEWS, 2004, 104 (05) :2507-2530