Synthesis of 8-substituted 1,5-diazabicyclo[3.2.1]octane derivatives via double aza-Michael addition of homopiperazine to 3-trifluoroacetyl-4 H -chromenes

The reaction of homopiperazine with 2-trifluoroacetyl-1H-benzo[f]chromenes affords 2-(1,5-diazabicyclo[3.2.1]octan-8-yl)-3-(trifluoromethyl)-2,3-dihydro-1H-benzo[f]chromen-3-ols, while 3-trifluoroacetyl-4H-chromenes give 2-[2-(1,5-diazabicyclo[3.2.1]octan-8-yl)ethyl]phenols. Both reactions are the first examples of synthesis of 1,5-diazabicyclo[3.2.1]octane core via double Michael addition and include cascade Michael addition/pyran ring opening/Michael addition.

Authors
Osipov D.V.1 , Melnikova I.V.1 , Osyanin V.A. 1, 2 , Lukashenko A.V.1 , Klimochkin Y.N.1
Publisher
Elsevier B.V.
Language
English
Pages
71-75
Status
Published
Volume
202
Year
2017
Organizations
  • 1 Samara State Technical University
  • 2 Peoples Friendship University of Russia
Keywords
homopiperazine; cascade reactions; 3-trifluoroacetyl-4H-chromenes; 1.5-Diazabicyclo[3.2.1]octane; aza-Michael reaction
Date of creation
10.07.2024
Date of change
10.07.2024
Short link
https://repository.rudn.ru/en/records/article/record/145886/
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