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 t2619-eo-0001" rel="references:#jhet2619-eo-0001"> and 4-hydroxy-1-phenylpyridin-2(1H)-ones t2619-eo-0025" rel="references:#jhet2619-eo-0025">. Compounds t2619-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 term6">acetic acid and polyphosphoric acid to give 3-acetyl-4-hydroxy-6-phenyl-6H-pyrano[3,2-c]pyridine-2,5-diones t2619-eo-0007" rel="references:#jhet2619-eo-0007"> in excellent yields. Compounds t2619-eo-0001" rel="references:#jhet2619-eo-0001"> and t2619-eo-0025" rel="references:#jhet2619-eo-0025"> can be iodinated with ttp://www.wiley.com/namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2619-eo-2000">term1 TH_term3">iodine and anhydrous ttp://www.wiley.com/namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2619-eo-2001">term1 TH_term3 TH_term6">sodium carbonate in boiling ttp://www.wiley.com/namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2619-eo-2002">term3">dioxane to give 4-hydroxy-3-iodo-6-phenyl-6H-pyrano[3,2-c]pyridine-2,5-diones t2619-eo-0013" rel="references:#jhet2619-eo-0013"> and 4-hydroxy-3-iodo-1-phenylpyridin-2(1H)-ones t2619-eo-0031" rel="references:#jhet2619-eo-0031">, respectively, in good yields. The structures were confirmed using infrared, term6">nuclear magnetic resonance , and elemental analysis.