Synthesis of Acetyl and Iodo Derivatives of 4-Hydroxy-6-phenyl-6H-pyrano[3,2-c]pyridine-2,5-diones and 4-Hydroxy-1-phenylpyridin-2(1H)-ones

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• 作者：B. P. Nikam and T. Kappe
• 刊名：Journal of Heterocyclic Chemistry
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：54
• 期：1
• 页码：546-550
• 全文大小：123K
• ISSN：1943-5193

文摘

A simple and efficient method has been described for the synthesis of acetyl and iodo derivatives of 4-hydroxy-6-phenyl-6H-pyrano[3,2-c]pyridine-2,5-diones het2619-eo-0001" rel="references:#jhet2619-eo-0001"> and 4-hydroxy-1-phenylpyridin-2(1H)-ones het2619-eo-0025" rel="references:#jhet2619-eo-0025">. Compounds het2619-eo-0001" rel="references:#jhet2619-eo-0001"> with phenyl and alkyl substituent at C(7) and C(8), respectively, can be easily acetylated by refluxing in a mixture of acetic acid and polyphosphoric acid to give 3-acetyl-4-hydroxy-6-phenyl-6H-pyrano[3,2-c]pyridine-2,5-diones het2619-eo-0007" rel="references:#jhet2619-eo-0007"> in excellent yields. Compounds het2619-eo-0001" rel="references:#jhet2619-eo-0001"> and het2619-eo-0025" rel="references:#jhet2619-eo-0025"> can be iodinated with Math/MathML" id="jhet2619-eo-2000">iodine and anhydrous het2619-eo-2001">sodium carbonate in boiling het2619-eo-2002">dioxane to give 4-hydroxy-3-iodo-6-phenyl-6H-pyrano[3,2-c]pyridine-2,5-diones het2619-eo-0013" rel="references:#jhet2619-eo-0013"> and 4-hydroxy-3-iodo-1-phenylpyridin-2(1H)-ones het2619-eo-0031" rel="references:#jhet2619-eo-0031">, respectively, in good yields. The structures were confirmed using infrared, nuclear magnetic resonance , and elemental analysis.