1431664-67-3Relevant articles and documents
A one-pot synthesis of tetrahydroisoquinolin-4-ols via a novel acid-catalyzed rearrangement of 5-aryloxazolidines
Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Ya.
, p. 2455 - 2457 (2013)
Benzaldehydes with electron-donating substituents react smoothly with a nonstabilized azomethine ylide derived from sarcosine and formaldehyde to form 5-aryloxazolidines as intermediates, which undergo rearrangement into 2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ols in high yields by simple heating with hydrochloric acid. This one-pot synthesis of tetrahydroisoquinolines can be considered as a formal [3+3] cycloaddition of the azomethine ylide to the aromatic aldehyde.
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.
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
