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Regio- and diastereoselective synthesis of novel polycyclic pyrrolo[2,1- a]isoquinolines bearing indeno[1,2- b]quinoxaline moieties by a three-component [3+2]-cycloaddition reaction

Matloubi Moghaddam, F ; Sharif University of Technology | 2020

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  1. Type of Document: Article
  2. DOI: 10.1055/s-0039-1690768
  3. Publisher: Georg Thieme Verlag , 2020
  4. Abstract:
  5. A regio- and diastereoselective synthesis of 2,3-dihydro-10b′ H -spiro[indeno[1,2- b ]quinoxaline-11,1′-pyrrolo[2,1- a ]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N -ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92%) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis. © 2020 Georg Thieme Verlag. All rights reserved
  6. Keywords:
  7. 1,3-dipolar cycloaddition ; Diastereoselectivity ; Indenoquinoxalines ; Multicomponent reaction ; Pyrroloisoquinolines ; Spiro compounds ; 2,3 dihydro 10b' H spiro[indeno[1,2 b]quinoxaline 11,1' pyrrolo[2,1 a]isoquinoline] 2',3' diylbis(phenylmethanone) derivative ; Indeno[1,2 b]quinoxaline derivative ; Isoquinolinium N ylide ; Pyrrolo[2,1 a]isoquinoline derivative ; Quinoxaline derivative ; Unclassified drug ; Chemical phenomena ; Chemical structure ; Chirality ; Cycloaddition ; Diastereoselective synthesis ; Physical chemistry ; Reaction analysis ; Reaction duration (chemistry) ; Regioselective synthesis ; Regioselectivity ; Stereochemistry ; Synthesis ; X ray diffraction
  8. Source: Synlett ; Volume 31, Issue 3 , 2020 , Pages 267-271
  9. URL: https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0039-1690768