Amberlyst-15 mediated synthesis of 2-substituted 2,3-dihydroquinazolin-4(1H)-ones and their crystal structure analysis

被引：65

作者：

Murthy, P. Vns ^{[2
]}

Rambabu, D. ^{[1
,2
]}

Krishna, G. Rama ^{[3
]}

Reddy, C. Malla ^{[3
]}

Prasad, K. R. S. ^{[2
]}

Rao, M. V. Basaveswara ^{[4
]}

Pal, Manojit ^{[1
]}

机构：

[1] Univ Hyderabad Campus, Inst Life Sci, Hyderabad 500046, Andhra Pradesh, India

[2] KL Univ, Dept Chem, Vaddeswaram 522502, Guntur, India

[3] Indian Inst Sci Educ & Res, Dept Chem Sci, Kolkata 741252, W Bengal, India

[4] Krishna Univ, Dept Chem, Machilipatnam 521001, AP, India

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 07期

关键词：

2,3-Dihydroquinazolin-4(1H)-ones, Aldehydes; Amberlyst-15; POT 3-COMPONENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; CATALYST; QUINAZOLIN-4(3H)-ONES; EFFICIENT; ACID;

D O I：

10.1016/j.tetlet.2011.12.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and clean method has been developed for the synthesis of 2-substituted 2,3-dihydroquinazolin-4(1H)-ones using Amberlyst-15 as a recyclable catalyst. A variety of dihydroquinazolinones were prepared from 2-aminobenzamide and aldehydes under mild conditions in excellent yields. Further structure elaboration of one compound and the crystal structure analysis and hydrogen bonding patterns of the two compounds prepared by using this methodology is presented. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：863 / 867

页数：5

共 29 条

[1] A novel method for the synthesis of 4(3H)-quinazolinones
Abdel-Jalil, RJ
Voelter, W
Saeed, M
[J]. TETRAHEDRON LETTERS, 2004, 45 (17) : 3475 - 3476
[2] ANTIBACTERIAL 2,3-DIHYDRO-2-(5-NITRO-2-THIENYL)-QUINAZOLIN-4(1H)-ONES
ALAIMO, RJ
RUSSELL, E
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (03) : 335 - &
[3] Boehringer Sohn C. H., 1964, French Patent, Patent No. [M 2588, 2588]
[4] 1-AMINOACYL-2,3-DIHYDRO-4(1H)-QUINAZOLINONE DERIVATIVES WITH CHOLERETIC AND ANTIFIBRILLATORY ACTIVITY
BONOLA, G
DARE, P
MAGISTRE.MJ
MASSARAN.E
SETNIKAR, I
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (06) : 1136 - &
[5] Gallium(III) triflate-catalyzed one-pot selective synthesis of 2 3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones
Chen, Jiuxi
Wu, Dengze
He, Fei
Liu, Miaochang
Wu, Huayue
Ding, Jinchang
Su, Weike
[J]. TETRAHEDRON LETTERS, 2008, 49 (23) : 3814 - 3818
[6] Eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-ones in ionic liquids or ionic liquid-water without additional catalyst
Chen, Jiuxi
Su, Weike
Wu, Huayue
Liu, Miaochang
Jin, Can
[J]. GREEN CHEMISTRY, 2007, 9 (09) : 972 - 975
[7] Direct Catalytic Asymmetric Synthesis of Cyclic Aminals from Aldehydes
Cheng, Xu
Vellalath, Sreekumar
Goddard, Richard
List, Benjamin
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (47) : 15786 - +
[8] Asymmetric synthesis of 2,3-dihydro-2-arylquinazolin-4-ones: Methodology and application to a potent fluorescent tubulin inhibitor with anticancer activity
Chinigo, Gary M.
Paige, Mikell
Grindrod, Scott
Hamel, Ernest
Dakshanamurthy, Sivanesan
Chruszcz, Maksymilian
Minor, Wladek
Brown, Milton L.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) : 4620 - 4631
[9] QUINAZOLINONE SULFONAMIDES AS DIURETIC AGENTS
COHEN, E
KLARBERG, B
VAUGHAN, JR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (20) : 5508 - 5509
[10] [bmim]HSO4: an efficient and reusable catalyst for one-pot three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones
Darvatkar, Nitin B.
Bhilare, Sachin V.
Deorukhkar, Amol R.
Raut, Dilip G.
Salunkhe, Manikrao M.
[J]. GREEN CHEMISTRY LETTERS AND REVIEWS, 2010, 3 (04) : 301 - 306

← 1 2 3 →