Synthesis of Indolizines by Dimerization of N-Propargylated Pyrroles via Allene Intermediates

Date

2021-03-01

Author

Kuzu, Burak
Gul, Sergen
Tan Uygun, Meltem
Mengeş, Nurettin
Balcı, Metin

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

186
views

0
downloads

Ten different N-propargyl pyrrole derivatives having various substituents at the C-2 position were synthesized. These derivatives were converted into indolizine derivatives by the [2+2] cycloaddition reaction of pyrrole N-allene, forming in situ, by heating in PrOH in basic medium. The structures were characterized by NMR and X-ray crystallography. The N-propargylated derivatives smoothly underwent intermolecular cyclizations to produce indolizine derivatives in good yields. We proposed a radical mechanism for the dimerization. Reaction of an allene product with butylated hydroxytoluene (BHT), a radical scavenger, did not give any dimerization product. This result supports the radical reaction.

URI

https://hdl.handle.net/11511/89755

Journal

CHEMISTRYSELECT

DOI

https://doi.org/10.1002/slct.202100045

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Synthesis of fused tetrazolone derivatives Ozcan, Sevil; Ekmekci, Zeynep; Mujde, Berk; Balcı, Metin (2013-01-01) New fused tetrazolone derivatives were synthesized using homophthalic and maleic anhydrides. Treatment of anhydrides with trimethylsilyl azide opened the lactone rings and formed the corresponding intermediates, which bore 1,3-dipole and dipolarophile functionalities in ortho positions. The intermediates partially underwent internal 1,3-dipolar cycloaddition to produce fused tetrazolone derivatives. When the carbonyl groups in anhydride were not conjugated with any double bond, then a triazine-fused tetrazo...
Synthesis of New Thienylene Pyrrole Monomers and Their Electropolymerizations Eken, Serap; Carbas, Buket Bezgin; Akdağ, Akın; Önal, Ahmet Muhtar (The Electrochemical Society, 2014-01-01) In this study, four new 2,5-dithienylpyrroles (SNS) 1-(3-fluoro-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-FPTP), 1-(3-chlorophenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-ClPTP), 1-(3-bromo-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-BrPTP) and 1-(4-bromo-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (p-BrPTP) containing meta and para substituted benzene ring at the nitrogen atom were synthesized via Paal-Knorr condensation of 1,4-di(2-thienyl)-1,4-butanedione with corresponding halo-substituted anilines. The mon...
Synthesis of dipyrrolo-diazepine derivatives via intramolecular alkyne cyclization Baskin, Dilges; Cetinkaya, Yasin; Balcı, Metin (2018-07-26) A regioselective approach was developed for the synthesis of dipyrrolo-diazepine derivatives. The synthetic route to dipyrrolo-diazepines first involves the synthesis of dipyrromethanes, followed by reaction of propargyl bromide in the presence of NaH to attach one alkyne functionality to the pyrrole nitrogen atom. Intramolecular heterocyclization with NaH in DMF between the alkyne functionality and pyrrole nitrogen atom gave the desired structures in good yields.
Synthesis of ferrocene substituted pyrrolidine derivatives via Et2Zn catalyzed 1 3 dipolar cycloaddition reactions of azomethine ylides Doğan, Özdemir (2001-05-01) Synthesis of ferrocene substituted pyrrolidine derivatives via diethylzinc catalyzed 1,3-dipolar cycloadditions of azomethine ylides is described. Azomethine ylides were generated from glycine methyl ester and ferrocenecarboxaldehyde by the 'imine tautomerization' method and trapped with dipolarophiles to give the corresponding cycloadducts in reasonable yields and high regio- and stereoselectivity.
SYNTHESIS OF BLOCK COPOLYMERS VIA ANION-TO-RADICAL TRANSFORMATION HAZER, B; CAKMAK, I; KUCUKYAVUZ, S; NUGAY, T (Elsevier BV, 1992-10-01) Synthesis of (methyl methacrylate)-styrene block copolymers was carried out using anion-to-radical transformation. For this purpose, living polystyryl anion, prepared by using a new anionic difunctional initiator, 1,5-di(2-(3,3-dimethyl butyl-1-lithio)naphthalene, was terminated by the addition of 4,4'-bromomethyl dibenzoyl peroxide. Polystyrene samples having peroxide terminal groups were then used as initiators in the polymerization of methyl methacrylate. Block copolymers were characterized by spectrosco...

Citation Formats

B. Kuzu, S. Gul, M. Tan Uygun, N. Mengeş, and M. Balcı, “Synthesis of Indolizines by Dimerization of N-Propargylated Pyrroles via Allene Intermediates,” CHEMISTRYSELECT, pp. 2366–2372, 2021, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/89755.