88953-56-4Relevant academic research and scientific papers
Synthesis of 6,12-Methanodibenzo[ c, f]azocines and 4-Aryltetrahydroisoquinolines from Aromatic Aldehydes
Buev, Evgeny M.,Stepanov, Maxim A.,Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Y.
supporting information, p. 631 - 635 (2020/01/31)
A methodology for the synthesis of 7,12-dihydro-5H-6,12-methanodibenzo[c,f]azocines from aromatic aldehydes and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine using catalysis by trifluoroacetic and perchloric acids is described. The developed protocol was applied for the synthesis of N-unsubstituted and N-methyl-4-aryltetrahydroisoquinolines.
Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines
Buev, Evgeny M.,Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Y.
supporting information, p. 1764 - 1767 (2016/05/19)
Nonstabilized azomethine ylides are easily trapped by anthraquinone to form stable spiro-oxazolidines, which have an unusual ability to undergo a cycloreversion in the presence of other dipolarophiles at 120-150°C. All tested recycloadditions with carbonyl compounds and electron-poor alkenes occurred in moderate to high yields (41-92%). Moreover, increasing the reaction temperature to 210°C made it possible to obtain adducts with low reactive dipolarophiles.
A one-pot synthesis of 4-aryl-2-methyl-1,2,3,4-tetrahydro-γ-carbolines from 5-aryloxazolidines and indoles via a Mannich/Friedel-Crafts sequence
Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Y.
, p. 6121 - 6124 (2015/02/02)
Benzaldehydes react smoothly with the nonstabilized azomethine ylide derived from sarcosine and formaldehyde to form 5-aryloxazolidines, which undergo ring-opening to give 2-(indol-3-ylmethylamino)-1-arylethanols in 69-79% yields on reaction with indoles in acetic acid. Their subsequent acid-catalyzed cyclization into 4-aryl-2-methyl-1,2,3,4-tetrahydro-γ-carbolines was performed in polyphosphoric acid in moderate yields. The latter can also be prepared directly from 5-aryloxazolidines and indoles in polyphosphoric acid.
Reaction of 5-aryloxazolidines with arylmagnesium bromides as a new route to N-benzyl-β-hydroxyphenethylamines as starting materials for the preparation of 4-aryl-1,2,3,4-tetrahydroisoquinolines
Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Ya.
, p. 2699 - 2702 (2013/06/26)
Benzaldehydes react smoothly with the non-stabilized azomethine ylide derived from sarcosine and formaldehyde to form 5-aryloxazolidines as intermediates, which undergo ring-opening to give N-benzyl-β- hydroxyphenethylamines in good yields by the action o
A simple two-step synthesis of 2-(alkylamino)-1-arylethanols, including racemic adrenaline, from aromatic aldehydes via 5-aryloxazolidines
Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Ya.
, p. 5869 - 5872 (2013/10/21)
Benzaldehydes react smoothly with nonstabilized azomethine ylides, generated in situ from sarcosine/formaldehyde or N-(methoxymethyl)-N- (trimethylsilylmethyl)benzylamine, to give 5-aryloxazolidines as intermediates. These were converted into 2-(alkylamino)-1-arylethanols in good yields by simple heating in methanol with hydrochloric acid, or by treatment with hydrazine hydrate in ethanol.
Neighbour Group Participation with Reductions and Hydride Abstractions
Moehre, H.,Kamper, Ch.
, p. 512 - 520 (2007/10/02)
The reduction of N-(2-hydroxyalkyl)lactams with diisobutylaluminium hydride and the hydride ion abstraction of the corresponding amino alcohols give under neighbour group participation the fused oxazolidines.
