Synthesis of New Derivatives of 4-(4,7,7-Trimethyl-7,8-dihydro-6m>Hm>-benzo[m>bm>]pyrimido[5,4-m>em>][1,4]thiazin-2-yl)morpholine

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• 作者：Azam Karimian ; Hossein Eshghi ; Mehdi Bakavoli and Ali Shiri
• 刊名：Journal of Heterocyclic Chemistry
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：54
• 期：1
• 页码：151-154
• 全文大小：316K
• ISSN：1943-5193

文摘

H_term4">Cyclocondensation of mlns:w="http://www.wiley.com/namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2556-eo-0001">m3">5-amino-6-methyl-2-morpholinopyrimidine-4-thiol (href="#jhet2556-eo-0001" rel="references:#jhet2556-eo-0001">) and mlns:w="http://www.wiley.com/namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2556-eo-0002">m3">2-bromo-5,5-dimethylcyclohexane-1,3-dione (href="#jhet2556-eo-0002" rel="references:#jhet2556-eo-0002">) under mild reaction condition afforded mlns:w="http://www.wiley.com/namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2556-eo-0003">m3">4,7,7-trimethyl-2-morpholino-7,8-dihydro-5m>Hm>-benzo[m>bm>]pyrimido[5,4-m>em>][1,4]thiazin-9(6m>Hm>)-one (href="#jhet2556-eo-0003" rel="references:#jhet2556-eo-0003">). The ¹H and ¹³C NMR data of compound (href="#jhet2556-eo-0003" rel="references:#jhet2556-eo-0003">) are demonstrated that this compound exists primarily in the enamino ketone form. Reaction of compound (href="#jhet2556-eo-0003" rel="references:#jhet2556-eo-0003">) with mlns:w="http://www.wiley.com/namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2556-eo-2004">m3">phosphorous oxychloride gave mlns:w="http://www.wiley.com/namespaces/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns:mml="http://www.w3.org/1998/Math/MathML" id="jhet2556-eo-0004">m3">4-(9-chloro-4,7,7-trimethyl-7,8-dihydro-6m>Hm>-benzo[m>bm>]pyrimido[5,4-m>em>][1,4]thiazin-2-yl)morpholine (href="#jhet2556-eo-0004" rel="references:#jhet2556-eo-0004">). m4">Nucleophilic substitution of chlorine atom of compound (href="#jhet2556-eo-0004" rel="references:#jhet2556-eo-0004">) with typical secondary amines in DMF and K₂CO₃ furnished the new substituted derivatives of 4-(4,7,7-trimethyl-7,8-dihydro-6m>Hm>-benzo[m>bm>]pyrimido[5,4-m>em>][1,4]thiazin-2-yl)morpholine (href="#jhet2556-eo-0006" rel="references:#jhet2556-eo-0006 #jhet2556-eo-0007 #jhet2556-eo-0008 #jhet2556-eo-0009 #jhet2556-eo-0010 #jhet2556-eo-0011 #jhet2556-eo-0012 #jhet2556-eo-0013">). All the synthesized products were characterized and confirmed by their spectroscopic and microanalytical data.