Bimolecular Condensation of 1-(para-tolyl)-and 1-(biphenyl-4-yl)-3,4,4-trichloro-3-buten-1-ones to 2,3,4,6-substituted 4Н-pyrans*
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Compounds of pyran series have been known for a long time, yet they still attract a steady interest due to the high biological activity caused by the affinity of pyran fragment towards various receptors [1, 2, 3]. The biological action of pyrans largely depend on the functional groups bonded to the heterocycle, which also define the possibilities of using these compounds for directed synthesis of useful products [4, 5, 6]. Functionally substituted pyrans are structural fragments of many natural biologically active compounds , pesticides , antibacterials [9, 10, 11], and antitumor drugs [12, 13]. Besides that, 4-methylene-4Н-pyrans are considered as promising materials for organic LED devices .
Various methods for the construction of pyran heterocycle are known, including those based on the use of unsaturated ketones. Thus, alkyl β,β-dichlorovinyl ketones, containing an activated methylene group, undergo crotonic condensation in the presence of anhydrous AlCl3 or Mg(ClO4)2...
Keywordsaryl trichloroallyl ketones guanidine pyrans condensation heterocyclization isomerization tautomerism
This work received financial support from the Belarusian Republican Foundation for Fundamental Research (grant Kh12СО-012) and the Siberian Branch of Russian Academy of Sciences (grant No. 21).
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