Abstract
A facile and versatile procedure has been explored for the synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4Hchromenes, pyrano[2,3-d]pyrimidines and 1,4-dihydropyrano[2,3-c]pyrazole-5-yl cyanides. This protocol employs the one-pot three-component condensation of aromatic aldehydes and malononitrile with 5,5-dimethyl-cyclohexane-1,3- dione, 1,3-dimethyl barbituric acid or 3-methyl-1-phenyl-2-pyrazolin-5-ones respectively in ethanol under the catalytic effect of triethylamine and ultrasonic-irradiation conditions. Simple manipulation, high reaction rates, improved yields, use of inexpensive and non-toxic catalyst, and also use of ethanol as a relatively environmentally benign solvent are the main advantages of this protocol.
Keywords: 4H-chromenes, pyrano[2, 3-d]pyrimidines, pyrano[2, 3-c]pyrazole, ultrasonic-irradiation, triethylamine, scaffolds, antibronchitics, microwave, electrochemically, induced
Letters in Organic Chemistry
Title:Ultrasonic-Promoted One-Pot Synthesis of 4H-chromenes, pyrano[2,3- d]pyrimidines, and 4H-pyrano[2,3-c]pyrazoles
Volume: 9 Issue: 6
Author(s): Davood Azarifar, Razieh Nejat-Yami, Fatemeh Sameri and Zahra Akrami
Affiliation:
Keywords: 4H-chromenes, pyrano[2, 3-d]pyrimidines, pyrano[2, 3-c]pyrazole, ultrasonic-irradiation, triethylamine, scaffolds, antibronchitics, microwave, electrochemically, induced
Abstract: A facile and versatile procedure has been explored for the synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4Hchromenes, pyrano[2,3-d]pyrimidines and 1,4-dihydropyrano[2,3-c]pyrazole-5-yl cyanides. This protocol employs the one-pot three-component condensation of aromatic aldehydes and malononitrile with 5,5-dimethyl-cyclohexane-1,3- dione, 1,3-dimethyl barbituric acid or 3-methyl-1-phenyl-2-pyrazolin-5-ones respectively in ethanol under the catalytic effect of triethylamine and ultrasonic-irradiation conditions. Simple manipulation, high reaction rates, improved yields, use of inexpensive and non-toxic catalyst, and also use of ethanol as a relatively environmentally benign solvent are the main advantages of this protocol.
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Cite this article as:
Azarifar Davood, Nejat-Yami Razieh, Sameri Fatemeh and Akrami Zahra, Ultrasonic-Promoted One-Pot Synthesis of 4H-chromenes, pyrano[2,3- d]pyrimidines, and 4H-pyrano[2,3-c]pyrazoles, Letters in Organic Chemistry 2012; 9 (6) . https://dx.doi.org/10.2174/157017812801322435
DOI https://dx.doi.org/10.2174/157017812801322435 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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