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

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Organocatalytic Diastereoselective Synthesis of Spiro[3-azabicyclo[3.1.0]hexanes] via 1,3-Dipolar Cycloaddition of Azomethine Ylides with Cyclopropenes. / Pronina, Yu. A.; Viktorov, N. B.; Selivanov, S. I.; Kornev, A. A.; Ponyaev, A. I.; Boitsov, V. M.; Stepakov, A. V.

In: Russian Journal of General Chemistry, Vol. 94, No. 4, 01.04.2024, p. 804-823.

Research output: Contribution to journal › Article › peer-review

Author

Pronina, Yu. A. ; Viktorov, N. B. ; Selivanov, S. I. ; Kornev, A. A. ; Ponyaev, A. I. ; Boitsov, V. M. ; Stepakov, A. V. / Organocatalytic Diastereoselective Synthesis of Spiro[3-azabicyclo[3.1.0]hexanes] via 1,3-Dipolar Cycloaddition of Azomethine Ylides with Cyclopropenes. In: Russian Journal of General Chemistry. 2024 ; Vol. 94, No. 4. pp. 804-823.

BibTeX

@article{8d52dac52852446a9f9d23da6d2b2270,

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

abstract = "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.",

keywords = "1, 3-dipolar cycloaddition, 3-azabicyclo[3.1.0]hexanes, acenaphthenequinone, azomethine ylides, cyclopropenes, isatins, organocatalysis, squaramides, 1,3-dipolar cycloaddition",

author = "Pronina, {Yu. A.} and Viktorov, {N. B.} and Selivanov, {S. I.} and Kornev, {A. A.} and Ponyaev, {A. I.} and Boitsov, {V. M.} and Stepakov, {A. V.}",

year = "2024",

month = apr,

day = "1",

doi = "10.1134/s107036322404008x",

language = "English",

volume = "94",

pages = "804--823",

journal = "Russian Journal of General Chemistry",

issn = "1070-3632",

publisher = "МАИК {"}Наука/Интерпериодика{"}",

number = "4",

}

RIS

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 -

ID: 121154338