scholarly journals Synthesis and transformation of 6-aminomethyl derivatives of 7-hydroxy-2'-fluoroisoflavones

2020 ◽  
Vol 8 (2) ◽  
pp. 203-213
Author(s):  
Olexandr Makarenko ◽  
Svitlana Bondarenko ◽  
Galyna Mrug ◽  
Mykhaylo Frasinyuk

Mannich aminomethylation of 8-methyl-7-hydroxy-2'-fluoroisoflavones applying bis-(N,N-dimethylamino)methane afforded C-6 substituted N,N-dimethylaminomethyl derivatives. Subsequent acetylation of these compounds in acetic anhydride in the presence of potassium acetate provided access to the corresponding acetoxymethyl derivatives that were converted to hydroxymethyl- and alkoxymethyl-substituted 7-hydroxyisoflavonoids. Addition of 3-(N,N-dimethylamino)-5,5-dimethyl-2-cyclohexen-1-one or 1,3-dimethyl-5-aminopyrazole with thermally generated ortho-quinone methides led to hetero-Diels–Alder or Michael adducts.

2016 ◽  
Vol 52 (7) ◽  
pp. 460-466 ◽  
Author(s):  
Galyna P. Mrug ◽  
Kostyantyn M. Kondratyuk ◽  
Svitlana P. Bondarenko ◽  
Mykhaylo S. Frasinyuk

2016 ◽  
Vol 71 (3) ◽  
pp. 267-271 ◽  
Author(s):  
Tariel V. Ghochikyan ◽  
Melanya A. Samvelyan ◽  
Vilik S. Harutyunyan ◽  
Edgar V. Harutyunyan ◽  
Andranik Petrosyan ◽  
...  

AbstractAn easy approach for the synthesis of various 5-substituted-3-(prop-2-ynyl)dihydrofuran-2(3H)-ones is described. As a method of choice, Mannich aminomethylation of terminal alkynes is adopted. The reaction works well with acyclic and cyclic secondary amines and provides the desired products, with good to very good yields.


2012 ◽  
Vol 9 (6) ◽  
pp. 633-637 ◽  
Author(s):  
Tomasz Plech ◽  
Monika Wujec ◽  
Urszula Kosikowska ◽  
Anna Malm ◽  
Magdalena Barylka ◽  
...  

ChemInform ◽  
2010 ◽  
Vol 28 (20) ◽  
pp. no-no
Author(s):  
M. M. MOVSUMZADE ◽  
N. A. NOVRUZOVA ◽  
SH. R. ALIEV

2002 ◽  
Vol 57 (6) ◽  
pp. 637-644 ◽  
Author(s):  
Krystyna Bogdanowicz-Szwed ◽  
Artur Budzowski

AbstractThe hetero-Diels-Alder reaction of 1-(2-furyl)-3-(dimethylamino)-2-propene-1-thione (diene) with maleic and fumaric acids, and β-nitrostyrenes yielded 3,4-dihydro-2H-thiopyran derivatives. Treatment of some of those cycloadducts with acetic acid caused elimination of dimethylamine yielding stable 2H-thiopyrans. Reaction of the diene with maleic anhydride furnished a cycloadduct which underwent spontaneous rearrangement to form an N,N-dimethylamide derivative. Cycloadditions of the diene to maleimide, N-phenylmaleimide, diethyl maleate, fumarate and butenolide, carried out in the presence of acetic anhydride,were followed by elimination of dimethylamine, afforded stable 2H-thiopyran derivatives.


1979 ◽  
Vol 10 (29) ◽  
Author(s):  
A. N. GRINEV ◽  
N. V. ARKHANGEL'SKAYA ◽  
G. YA. URETSKAYA ◽  
A. A. STOLYARCHUK ◽  
P. A. GALENKO-YAROSHEVSKII

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