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

页码：1144 / 1150

页数：7

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