Synthesis of tricyclic quinazolinones via intramolecular cyclization of 3-(2-aminoalkyl)-2-(phenylamino)quinazolin-4(3H)-ones

被引：4

作者：

Yang, Xuhong ^{[1
]}

Wu, Minghu ^{[1
]}

Sun, Shaofa ^{[1
]}

Huang, Changfeng ^{[2
]}

Guo, Haibing ^{[1
]}

Wang, Jian ^{[1
]}

Lee, John ^{[3
]}

Xing, Yalan ^{[3
]}

机构：

[1] Hubei Univ Sci & Technol, Hubei Collaborat Innovat Ctr Nonpower Nucl Techno, Coll Neuclear Technol Chem & Biol, Xianning 437100, Peoples R China

[2] W Virginia Univ, Bennett Dept Chem, Morgantown, WV 26506 USA

[3] William Paterson Univ, Dept Chem, 300 Pompton Rd, Wayne, NJ 07470 USA

来源：

MOLECULAR DIVERSITY | 2016年 / 20卷 / 02期

基金：

中国国家自然科学基金;

关键词：

Tricyclic quinazoline; Intramolecular cyclization; Guanidines; AMIDINES;

D O I：

10.1007/s11030-015-9636-9

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Bioactive tricyclic quinazolines class of 3,4-dihydro-1H-pyrimido[2,1-b]quinazolin-6(2H)-ones I and 2,3-dihydroimidazo[2,1-b]quinazolin-5(1H)-ones II were synthesized by the formic acid-catalyzed intramolecular cyclization of 3-(2-aminoalkyl)-2-(phenylamino)quinazolin-4(3H)-ones 1 in high yields. A plausible mechanism of the cyclization step is proposed.

引用

页码：551 / 556

页数：6

共 16 条

[1] [Anonymous], 2008, ANGEW CHEM
[2] The chemistry and biology of organic guanidine derivatives
Berlinck, Roberto G. S.
Burtoloso, Antonio Carlos B.
Kossuga, Miriam H.
[J]. NATURAL PRODUCT REPORTS, 2008, 25 (05) : 919 - 954
[3] Molecular recognition of oxoanions based on guanidinium receptors
Blondeau, Pascal
Segura, Margarita
Perez-Fernandez, Ruth
de Mendoza, Javier
[J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (02) : 198 - 210
[4] STUDIES ON 1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDES-VII AND QUINAZOLINONES-IV - SYNTHESIS OF NOVEL BUILT-IN HYDROXYGUANIDINE TRICYCLES AS POTENTIAL ANTICANCER AGENTS
CHERN, JW
LIAW, YC
CHEN, CS
RONG, JG
HUANG, CL
CHAN, CH
WANG, AHJ
[J]. HETEROCYCLES, 1993, 36 (05) : 1091 - 1103
[5] Enantioselective total synthesis of batzelladine F: Structural revision and stereochemical definition
Cohen, F
Overman, LE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) : 10782 - 10783
[6] Coles MP, 2006, DALTON T, P985, DOI 10.1039/b515490a
[7] Synthesis, in vitro antiproliferative activity and DNA-interaction of benzimidazoquinazoline derivatives as potential anti-tumor agents
Dalla Via, L
Gia, O
Magno, SM
Da Settimo, A
Marini, AM
Primofiore, G
Da Settimo, F
Salerno, S
[J]. FARMACO, 2001, 56 (03): : 159 - 167
[8] SYNTHESIS OF 4(3H)-QUINAZOLINONES FROM DERIVATIVES OF METHYL 2-ISOTHIOCYANATOBENZOATE
DEAN, WD
PAPADOPOULOS, EP
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (05) : 1117 - 1124
[9] AMIDINES .2. NEW CLASS OF ANTIHYPERTENSIVE AGENTS - 1,2,3,5-TETRAHYDROIMIDAZO[2,1-B]QUINAZOLINES
JEN, T
PETTA, J
HELT, A
DIENEL, B
LOEV, B
BOWMAN, H
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (07) : 727 - &
[10] Radical Synthesis of Guanidines from N-Acyl Cyanamides
Larraufie, Marie-Helene
Ollivier, Cyril
Fensterbank, Louis
Malacria, Max
Lacote, Emmanuel
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) : 2178 - 2181

← 1 2 →