Green One Pot Solvent-Free Synthesis of Pyrano[2,3-c]Pyrazoles and Pyrazolo[1,5-a]Pyrimidines

被引：92

作者：

Al-Matar, Hamad M. ^{[1
]}

Khalil, Khaled D. ^{[2
]}

Adam, Aisha Y. ^{[1
]}

Elnagdi, Mohamed H. ^{[1
]}

机构：

[1] Kuwait Univ, Fac Sci, Dept Chem, Safat 13060, Kuwait

[2] Cairo Univ, Fac Sci, Dept Chem, Giza 12613, Egypt

来源：

MOLECULES | 2010年 / 15卷 / 09期

关键词：

pyranopyrazole; multi-component synthesis; aminopyrazolinone; pyrazolo[1,5-a]pyrimidine; cyanoacetic acetic anhydride; NOE difference experiments; HETEROCYCLIC SYNTHESIS; MOLECULAR-STRUCTURE; NITRILES; DERIVATIVES; REAGENTS;

D O I：

10.3390/molecules15096619

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：

Pyrano[2,3-c]pyrazoles are obtained via mixing ethyl acetoacetate, hydrazine hydrate, aldehydes or ketones and malononitrile in the absence of solvent. These same products were also obtained by reacting arylidenemalononitriles 3 with 3-methyl-2-pyrazolin-5-ones. NOE difference experiments confirmed that these products exist solely in the 2H form. Similar treatments of 3-amino-2-pyrazolin-5-one with arylidene-malononitrile afforded adduct 6. Similarly mixing ethyl cyanoacetate, hydrazine hydrate, aldehydes, with malononitrile gave the same product 6. A novel synthesis of 4-oxo-4H-pyrano[2,3-c]pyrazole (8) could be achieved via reacting 3-methyl-2-pyrazolin-5-one with a mixture of cyanoacetic acid and acetic anhydride. Similar treatment of 3-aminopyrazole 11 with the benzylidene-malononitrile produced the pyrazolo[2,3-a]pyrimidines 12a,b.

引用

页码：6619 / 6629

页数：11

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