Show/Hide Menu
Hide/Show Apps
Logout
Türkçe
Türkçe
Search
Search
Login
Login
OpenMETU
OpenMETU
About
About
Open Science Policy
Open Science Policy
Open Access Guideline
Open Access Guideline
Postgraduate Thesis Guideline
Postgraduate Thesis Guideline
Communities & Collections
Communities & Collections
Help
Help
Frequently Asked Questions
Frequently Asked Questions
Guides
Guides
Thesis submission
Thesis submission
MS without thesis term project submission
MS without thesis term project submission
Publication submission with DOI
Publication submission with DOI
Publication submission
Publication submission
Supporting Information
Supporting Information
General Information
General Information
Copyright, Embargo and License
Copyright, Embargo and License
Contact us
Contact us
Synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from 2-(2-bromoallyl)-1,3-dicarbonyl compounds
Date
2002-12-02
Author
Demir, Ayhan Sıtkı
Akhmedov, IM
Sesenoglu, O
Metadata
Show full item record
This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
.
Item Usage Stats
254
views
0
downloads
Cite This
2-(2-Bromoallyl)-1,3-dicarbonyl compounds are converted into beta-enamino, beta-hydrazino esters and ketones, followed by base-promoted cyclization, leading to the formation of the corresponding 1,2,3,5-tetrasubstituted pyrroles. 1,2,4- and 1,2,3,4-Substituted pyrroles are also isolated as minor products. Starting from the 2-(2-bromoallyl)-cyclohexane-1,3-dione the corresponding tetrahydro indolone is prepared in good yield.
Subject Keywords
Organic Chemistry
,
Biochemistry
,
Drug Discovery
URI
https://hdl.handle.net/11511/51515
Journal
TETRAHEDRON
DOI
https://doi.org/10.1016/s0040-4020(02)01298-x
Collections
Department of Chemistry, Article
Suggestions
OpenMETU
Core
Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones
Demir, Ayhan Sıtkı; Aybey, Asuman (Elsevier BV, 2008-12-01)
The alpha-acetoxylation of indanones and tetralones by using Mn(OAc)(3) followed by the enzyme catalyzed kinetic resolution of acetoxy ketones furnished both of the enantiomers of alpha-acetoxy ketones in good chemical and optical yields. The Baeyer-Villiger oxidation of alpha-acetoxy ketones with m-CPBA, CF(3)SO(3)H, and CH(2)O(2), at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords ph...
Synthesis of various camphor-based chiral pyridine derivatives
Tanyeli, Cihangir; Isik, M (Elsevier BV, 2004-07-19)
(+)-beta-Hydroxymethylenecamphor 1 and enamines 2a-e were transformed into chiral camphor-based pyridine derivatives 3a-e via a tandem condensation reaction in good yields.
Reactions of acyl phosphonates with organoaluminum reagents: a new method for the synthesis of secondary and tertiary alpha-hydroxy phosphonates
Seven, Ozlem; Polat-Cakir, Sidika; Hossain, Md. Shakhawoat; Emrullahoglu, Mustafa; Demir, Ayhan Sıtkı (Elsevier BV, 2011-05-13)
The reactions of organoaluminum reagents (trimethylaluminum, triethylaluminum, etc.) with aryl and alkyl acyl phosphonates, which lead to the formation of alpha-hydroxy phosphonates in moderate to good yields, are reported. This method provides easy access to secondary and tertiary alpha-hydroxy phosphonates depending on the reaction conditions. The reactions of triethylaluminum with a series of acyl phosphonates at 0 degrees C gave the secondary alpha-hydroxy phosphonates, while at -100 degrees C they affo...
A novel synthesis of 1,2,4-oxadiazoles and isoxazoles
KIVRAK, Arif; Zora, Metin (Elsevier BV, 2014-01-28)
A novel synthesis of 1,2,4-oxadiazoles and isoxazoles is described by utilizing the reactions between amidoximes and alpha,beta-alkynic aldehydes and/or ketones. Conjugate addition products, obtained from amidoximes and alpha,beta-alkynic aldehydes and/or ketones, afford 1,2,4-oxadiazoles and isoxazoles when treated with bases and acids, respectively. 1,2,4-Oxadiazoles can also be synthesized directly from amidoximes and alpha,beta-alkynic aldehydes in a one-pot manner under basic conditions. The reactions ...
Coupling of cyclopropylcarbene-chromium complex with ferrocenyl alkynes: synthesis of 5-ferrocenyl-5-hydroxy-2-cyclopentenones and 4-ferrocenyl-4-cyclopentene-1,3-diones
Zora, Metin; Bueyuekguengoer, Orhan (Elsevier BV, 2007-05-07)
The coupling of ferrocenyl alkynes with cyclopropylcarbene-chromium complex leads to ferrocenyl-substituted 2-cyclopentenones with or without a hydroxy substituent, namely 4-cyclopentene-1,3-diones, 2-cyclobutenones, and alpha, beta-unsaturated aldehydes in varying amounts. The reaction initially produces a cyclopentadienone intermediate, then to the double bond of which, bearing a ferrocenyl group, addition of water occurs to afford hydroxy-substituted 2-cyclopentenones. In all the products, the hydroxy gr...
Citation Formats
IEEE
ACM
APA
CHICAGO
MLA
BibTeX
A. S. Demir, I. Akhmedov, and O. Sesenoglu, “Synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from 2-(2-bromoallyl)-1,3-dicarbonyl compounds,”
TETRAHEDRON
, pp. 9793–9799, 2002, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51515.