Condensation Reactions of 2-Aminobenzohydrazide with Various Carbonyl Compounds

被引：7
作者：
El-Shaieb, Kamal M. [1 ]
Ameen, Mohamed A. [1 ]
Abdel-Latif, Fathy F. [1 ]
Mohamed, Asmaa H. [1 ]
机构：
[1] Menia Univ, Dept Chem, Fac Sci, El Minia, Egypt
来源：
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 2012年 / 67卷 / 11期
关键词：
Quinazolines; Aminobenzohydrazide; Aldehydes; Ketones; Anhydrides; Hydrazones; TYROSINE KINASE INHIBITORS; GROWTH-FACTOR RECEPTOR; BIOLOGICAL EVALUATION; DERIVATIVES; POTENT; EFFICIENT; SERIES; SPIRO;
D O I：
10.5560/ZNB.2012-0202
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Technical iodine was found to catalyze the condensation between 2-aminobenzohydrazide (1) and some aldehydes and ketones in absolute ethanol under mild conditions to afford hydrazone and quinazoline derivatives, respectively. Condensation of 1 with terephthalaldehyde (2) in 1: 1 molar ratios afforded the hydrazone 3, while hydrazone 4 was formed on using a double molar ratio of 1. On the other hand, compound 1 condensed with 4-formyl [2.2]paracyclophane (5) to give the hydrazone 6. However, spiro-quinazolines 8, 10, 12, and 14 were formed when compound 1 reacted with ketones such as N-benzylpiperidone (7), indane-1,2,3-trione (9), cyclohexane-1,2-dione (11), and dimedone (13), respectively. Treatment of 1 with tetrabromophthalic anhydride (TBPA, 18) and pyromellitic dianhydride (PMDA, 20) furnished phthalazino-quinazoline 19 and 21, respectively. The products were fully characterized according to their spectral analyses. The mechanisms of formation of the products have been rationalized.
引用
收藏
页码：1144 / 1150
页数：7
相关论文
共 50 条
[41]   Synthesis of Chromenes by Cyclizative Condensation of Phenols with α,β-Unsaturated Carbonyl Compounds over Halide Cluster Catalysts [J].
Nagashima, Sayoko ;
Takahashi, Toru ;
Nasrin, Noor ;
Kamiguchi, Satoshi ;
Chihara, Teiji .
CHEMISTRY LETTERS, 2016, 45 (11) :1321-1323
[42]   Acid Catalysts Based on Mesoporous Aromatic Frameworks in Aldol Condensation of Furfural with Some Carbonyl Compounds [J].
M. Yu. Talanova ;
V. A. Yarchak ;
E. A. Karakhanov .
Russian Journal of Applied Chemistry, 2019, 92 :857-864
[43]   A selective solvent-free self-condensation of carbonyl compounds utilizing microwave irradiation [J].
Sharma, Lalit Kumar ;
Kim, Kyung Bo ;
Elliott, Gregory I. .
GREEN CHEMISTRY, 2011, 13 (06) :1546-1549
[44]   The Formation of 2-Isoxazolines in the Reactions of α,β-Unsaturated Carbonyl Compounds with Hydroxylamine and its Derivatives-A Critical Review [J].
Drosik, Olga Kinga ;
Suwinski, Jerzy Wiktor .
CURRENT ORGANIC CHEMISTRY, 2018, 22 (04) :345-361
[45]   Efficient chemoselective addition of Grignard reagents to carbonyl compounds in 2-methyltetrahydrofuran [J].
Zhong, Weihui ;
Wu, Yaotiao ;
Zhang, Xingxian .
JOURNAL OF CHEMICAL RESEARCH, 2009, (06) :370-373
[46]   Efficient method for the reduction of carbonyl compounds by triethylsilane catalyzed by PdCl2 [J].
Mirza-Aghayan, Maryam ;
Boukherroub, Rabah ;
Rahimifard, Mahshid .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (24) :3567-3570
[47]   Nucleophilic Iododifluoromethylation of Carbonyl Compounds Using Difluoromethyl 2-Pyridyl Sulfone [J].
Miao, Wenjun ;
Ni, Chuanfa ;
Zhao, Yanchuan ;
Hu, Jinbo .
ORGANIC LETTERS, 2016, 18 (11) :2766-2769
[48]   PdBr2-Catalyzed Acetal Formation of Carbonyl Compounds Using Diazophenanthrenequinone: Utility of 9,10-Phenanthrenedioxyacetal [J].
Kitamura, Mitsuru ;
Fujimura, Ryo ;
Nishimura, Tomoaki ;
Takahashi, Shuhei ;
Shimooka, Hirokazu ;
Okauchi, Tatsuo .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (33) :5319-5322
[49]   Clay Catalyzed Reactions of Indole and its Methyl Derivatives with α, β-unsaturated Carbonyl Compounds [J].
Dasbasi, Teslima ;
Abdullah, Meysun I. .
CROATICA CHEMICA ACTA, 2014, 87 (02) :137-142
[50]   2-Nitro-cyclopropyl-1-carbonyl Compounds from Unsaturated Carbonyl Compounds and Nitromethane via Enolonium Species [J].
Ghosh, Asit ;
Lipisa, Yuriy B. ;
Fridman, Natalia ;
Szpilman, Alex M. .
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (04) :1977-1987
12345