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A novel and efficient four-component synthesis of chromen–based dithiocarbamate derivatives by homogeneous catalysts under solvent-free conditions
, Article Synthetic Communications ; Volume 51, Issue 12 , 2021 , Pages 1825-1833 ; 00397911 (ISSN) ; Goudarzi, M ; Mohammadzadeh Dezag, H ; Sharif University of Technology
Bellwether Publishing, Ltd
2021
Abstract
An efficient and one-pot procedure is described for the synthesis of a variety of derivatives of 1,2-dihydrobenzo[f]chromen-3-ones and 3,4-dihydrochromen-2-ones under solvent-free conditions via a pseudo-four-component domino reaction of acetic anhydride, aryl aldehydes, glycine-based dithiocarbamates, and phenols/naphthols in the presence of l-proline and H4[Si(W3O10)4].xH2O as green catalysts. All products were made under the green strategy for the synthesis of corresponding products with excellent yields (up to 94%) and diastereoselectivity. © 2021 Taylor & Francis Group, LLC
New Methods for the Synthesis of N,S‑Heterocycles and Dithiocarbamates Using Amine Derivatives and CS2
, Ph.D. Dissertation Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor)
Abstract
In the first section, a novel and efficient multicomponent reaction for the synthesis of polysubstituted pyrrolidine derivatives is described under catalyst-free conditions using unltrasonic irradiation. The reactions were performed via a one-pot four-component condensation of secondary amines, carbon disulfide, isocyanides, and gem-dicyano olefins at room temperature to afford polysubstituted pyrrolidines diastereoselectively in 56-96% yields. This is the first report of Mumm-type rearrangement with dithiocarbamates followed by intramolecular cyclization which lead to the preparation of the key structure of pyrrolidine.In the second section, an efficient and unprecedented green protocol...
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...