TY - JOUR

T1 - Organocatalytic Diastereoselective Synthesis of Spiro[3-azabicyclo[3.1.0]hexanes] via 1,3-Dipolar Cycloaddition of Azomethine Ylides with Cyclopropenes

AU - Pronina, Yu. A.

AU - Viktorov, N. B.

AU - Selivanov, S. I.

AU - Kornev, A. A.

AU - Ponyaev, A. I.

AU - Boitsov, V. M.

AU - Stepakov, A. V.

PY - 2024/4/1

Y1 - 2024/4/1

N2 - A three-component organocatalytic reaction of 1,3-dipolar cycloaddition between the in situ generated azomethine ylides and 3-substituted 1,2-diphenylcyclopropenes is described. The azomethine ylides have been generated via condensation of aromatic compounds (such as isatins and acenaphthenequinone) with benzylamines. The reaction has afforded derivatives of 3-azabicyclo[3.1.0]hexane, spiro-fused with the fragments of 2-oxindole and acenaphthylene-1(2H)-one. The cycloadducts have been obtained with yield up to 91 mainly as individual diastereomers. The influence of bifunctional squaramide-based organocatalysts on the course of these three-component reactions has been investigated. Antiproliferative activity of selected synthesized compounds with respect to the human erythromyelosis (K562) and melanoma (Sk-mel-2) cell lines has been assessed in vitro by means of MTS analysis.

AB - A three-component organocatalytic reaction of 1,3-dipolar cycloaddition between the in situ generated azomethine ylides and 3-substituted 1,2-diphenylcyclopropenes is described. The azomethine ylides have been generated via condensation of aromatic compounds (such as isatins and acenaphthenequinone) with benzylamines. The reaction has afforded derivatives of 3-azabicyclo[3.1.0]hexane, spiro-fused with the fragments of 2-oxindole and acenaphthylene-1(2H)-one. The cycloadducts have been obtained with yield up to 91 mainly as individual diastereomers. The influence of bifunctional squaramide-based organocatalysts on the course of these three-component reactions has been investigated. Antiproliferative activity of selected synthesized compounds with respect to the human erythromyelosis (K562) and melanoma (Sk-mel-2) cell lines has been assessed in vitro by means of MTS analysis.

KW - 1

KW - 3-dipolar cycloaddition

KW - 3-azabicyclo[3.1.0]hexanes

KW - acenaphthenequinone

KW - azomethine ylides

KW - cyclopropenes

KW - isatins

KW - organocatalysis

KW - squaramides

KW - 1,3-dipolar cycloaddition

UR - https://www.mendeley.com/catalogue/5f825015-548c-3603-ac5d-835a13deee66/

U2 - 10.1134/s107036322404008x

DO - 10.1134/s107036322404008x

M3 - Article

VL - 94

SP - 804

EP - 823

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

SN - 1070-3632

IS - 4

ER -