Synthesis of polycyclic imidazo[1,4]thiazine derivatives by an ANRORC domino reaction

10bH-6-Oxa-1-thia-3a,5-diazaacephenanthrylenes can be easily obtained by a sodium hydrogen carbonate catalyzed anionic domino reaction of thiazolium salts with salicylic aldehydes. It is presumed that the domino sequence includes Kröhnke condensation, nucleophilic cyclization, and ANRORC (addition of nucleophile/ring opening/ring closure) steps. To the best of our knowledge, this is a first example of a multistep anionic domino reaction incorporating an ANRORC transformation. The initial generality of the method is demonstrated by using 3-hydroxypyridine-2-carbaldehyde as a carbonyl component. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Authors
Voskressensky L.G. 1 , Festa A.A. 1 , Sokolova E.A. 1 , Khrustalev V.N.2 , Varlamov A.V. 1
Journal
European Journal of Organic Chemistry
Number of issue
31
Language
English
Pages
6124-6126
Status
Published
Link
External link
DOI
10.1002/ejoc.201200895
Year
2012
Organizations
  • 1 Peoples Friendship University of Russia, 6, Miklukho-Maklaia St., Moscow 117198, Russian Federation
  • 2 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St. 28, B-334, Moscow 119991, Russian Federation
Keywords
Cyclization; Domino reactions; Fused-ring systems; Heterocycles; Sulfur
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/2247/
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