Synthesis of Various Schiff Bases Containing Isoxazole Ring and Their Applications with Thioglycollic Acid and Diverse Phosphorus Reagents

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• 作者：Abeer A. Shady ; Sherifa M. Abu Bakr and Maha D. Khidre
• 刊名：Journal of Heterocyclic Chemistry
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：54
• 期：1
• 页码：71-79
• 全文大小：776K
• ISSN：1943-5193

文摘

A series of Schiff bases bearing isoxazole and pyrazole rings were synthesized. Application of thioglycollic acid on two selective synthesized Schiff bases afforded the corresponding thiazolidin-4-one derivatives. On the other hand, following the multicomponents one-pot Kabachnik– Fields reaction, the Schiff base generated in situ from namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2541-eo-0023">4-chlorobenzaldehyde and namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2541-eo-0001">5-methyl isoxazol-3-amine was trapped by phosphorus reagents to produce the corresponding amino phosphonates in moderate yields. However, the latter products could also be obtained in better yields (≥78%) by directly applying the dialkylphosphites to a selective synthesized Schiff base. Similarly, a series of α-aminophosphonates could be obtained from namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2541-eo-0003">5-chloro-3-methyl-1H-pyrazol-4-carbaldehyde, 5-methylisoxazol-3-amine, and phosphorus reagents. Moreover, applying hexaalkyl triamido phosphites to the namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2541-eo-2007">N-(4-chlorobenzylidene)-5-methylisoxazol-3-amine in ethanol afforded methylphosphonic diamide derivatives, whereas namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2541-eo-2009">N-((5-chloro-3-methyl-1H-pyrazol-4-yl)methylene)-5-methylisoxazol-3-amine underwent dechlorination through reaction with hexaalkyl triamido phosphites to give the respective amine derivatives.