Synthesis and reactions of “biginelli‐compounds”. Part I

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書誌事項

公開日
1989-01
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/jhet.5570260112
公開者
Wiley

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<jats:title>Abstract</jats:title><jats:p>Various reactions of 2‐oxo(or thioxo)‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylic acid derivatives (Biginelli‐compounds) were investigated. The site of methylation and acylation on 6‐methyl‐4‐phenyl‐2‐thioxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylic acid ethyl ester <jats:bold>1a</jats:bold> and its 2‐oxo derivative <jats:bold>9a</jats:bold> was studied. The synthesis of pyrimido[2,3‐<jats:italic>b</jats:italic>]thiazines and thiazolo[3,2‐<jats:italic>a</jats:italic>]pyrimidines was accomplished by condensation of <jats:bold>1a</jats:bold> with 1,3‐and 1,2‐dielectrophiles. A Dimroth‐like rearrangement yielding 6<jats:italic>H</jats:italic>‐1,3‐thiazines can be observed when <jats:bold>1a</jats:bold> was treated with dimethylformamide and phosphorus oxychloride. The formation of indeno[1,2‐<jats:italic>d</jats:italic>]pyrimidines can be achieved by intramolecular Friedl‐Crafts acylation of <jats:bold>9a</jats:bold> and <jats:bold>13</jats:bold>, respectively. Finally a route for the preparation of 4,6‐disubstituted‐pyrimidine‐5‐carbonitriles is presented, starting with Biginelli‐compound <jats:bold>25</jats:bold>.</jats:p>

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