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Catalyst-Free three-component synthesis of spirobenzimidazolidines bearing an indole scaffold
, Article Synlett ; Volume 29, Issue 17 , 2018 , Pages 2301-2305 ; 09365214 (ISSN) ; Moafi, A ; Zamani, Z ; Daneshfar, M ; Sharif University of Technology
Georg Thieme Verlag
2018
Abstract
An efficient catalyst-free one-pot three-component reaction was developed for the synthesis of a new family of N- A nd S-containing spirocyclic compounds. Various derivatives of spirobenzimidazolidine containing an indole scaffold were synthesized for the first time in a modestly toxic solvent and under mild reaction conditions. The reaction times were of the order of several minutes, and all the products were obtained in moderate to high yields (overall yields 58-80%). © Georg Thieme Verlag Stuttgart New York
Synthesis and Characterization of some Nitrogen Containing Heterocyclic Compounds Using Synthetic Intermediat of Isatin Analogues
, M.Sc. Thesis Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor)
Abstract
An efficient catalyst-free one-pot three-component reaction was developed for the synthesis of a new family of N- and S-containing spirocyclic compounds.Various derivatives of spirobenzimidazolidine containing an indole scaffold were synthesized for the first time in a modestly toxic solvent and under mild reaction conditions. The reaction times were of the order of several minutes, and all the products were obtained in moderate to high yields (overall yields 58–80%)
Synthesis of Spiro Heterocyclic Compounds by Using Isatin Based 1,3-Dipolar
, M.Sc. Thesis Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor)
Abstract
Today, heterocycle compounds have become increasingly important in organic chemistry syntheses. Many extracellular compounds have a confirmed biological property. Due to the high bioactivity of these compounds, the development of their synthetic methods has received considerable attention and numerous reports have been published on their synthesis. One of the most commonly used examples is terazosin. It was first marketed as a blood pressure lowering drug but was later used in the treatment of benign prostate gland.Another important class of these compounds may be the different derivatives of the pyrimidine molecule used in the treatment of cancer. The use of hetero- cyclic compounds is not...
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
, Article Synlett ; Volume 31, Issue 3 , 2020 , Pages 267-271 ; Moafi, A ; Jafari, B ; Vilinger, A ; Langer, P ; Sharif University of Technology
Georg Thieme Verlag
2020
Abstract
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
Diastereoselective construction of a functionalized dihydro-pyridazine-based spirooxindole scaffold: Via C-3 umpolung of isatin N, N ′-cyclic azomethine imine
, Article New Journal of Chemistry ; Volume 43, Issue 26 , 2019 , Pages 10318-10323 ; 11440546 (ISSN) ; Eslami, M ; Siahpoosh, A ; Hoda, G ; Sharif University of Technology
Royal Society of Chemistry
2019
Abstract
Herein, functionalized spiro[indoline-3,5′-pyrazolo[1,2-a]pyridazine]-7′-carbonitrile containing two contiguous chiral stereocenters was efficiently synthesized in a satisfactory yield (up to 91% yield) and with excellent diastereoselectivity. We have reached this satisfactory yield by DABCO-catalyzed [3+3] annulation reactions of an isatin N,N′-cyclic azomethine imine 1,3-dipole with a Knoevenagel intermediate in dichloromethane (DCM) as solvent at ambient temperature; this was an entirely new strategy for creating one quaternary stereogenic center at the position-3 of an oxindole structure using an abnormal tandem Michael addition, N-cyclization, and a unique approach via the azomethine...
Diastereoselective construction of a functionalized dihydro-pyridazine-based spirooxindole scaffold: via C-3 umpolung of isatin N, N ′-cyclic azomethine imine
, Article New Journal of Chemistry ; Volume 43, Issue 26 , 2019 , Pages 10318-10323 ; 11440546 (ISSN) ; Eslami, M ; Siahpoosh, A ; Hoda, G ; Sharif University of Technology
Royal Society of Chemistry
2019
Abstract
Herein, functionalized spiro[indoline-3,5′-pyrazolo[1,2-a]pyridazine]-7′-carbonitrile containing two contiguous chiral stereocenters was efficiently synthesized in a satisfactory yield (up to 91% yield) and with excellent diastereoselectivity. We have reached this satisfactory yield by DABCO-catalyzed [3+3] annulation reactions of an isatin N,N′-cyclic azomethine imine 1,3-dipole with a Knoevenagel intermediate in dichloromethane (DCM) as solvent at ambient temperature; this was an entirely new strategy for creating one quaternary stereogenic center at the position-3 of an oxindole structure using an abnormal tandem Michael addition, N-cyclization, and a unique approach via the azomethine...