Synthesis of dipyrrolo-diazepine derivatives via intramolecular alkyne cyclization

2018-07-26
Baskin, Dilges
Cetinkaya, Yasin
Balcı, Metin
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.

Suggestions

Reaction of Metal-Carbene Complexes with Cyclobutenediones: The First General C-C Bond Insertion Reaction for Fischer Carbene Complexes
Zora, Metin (American Chemical Society (ACS), 1993-01-01)
Alkylcarbene-chromium complexes react with cyclobutenediones to give 2-alkoxy-4-cyclopentene-1,3-diones in moderate yield, accompanied by varying amounts of 4-cyclopentene-1,3-dione derivatives which result from reduction of the initial product by the chromium byproduct. The reaction is general for a variety of cyclobutenedione derivatives with alkoxy, alkyl, or aryl substituents. The major products of the reaction between arylcarbene complexes and cyclobutenediones are 5-alkylidenefuranone derivatives. A m...
Selective synthesis of N-substituted pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives via alkyne cyclization
Cetinkaya, Yasin; Balcı, Metin (2014-12-03)
A novel and efficient synthesis of N-substituted pyrrolo-pyrazinone derivatives has been developed. A trichloroacetyl group connected to the pyrrole ring was converted into the desired carboxamide derivatives. Promoted by NaH, the pyrrole carboxamide derivatives underwent a tandem reaction with propargyl bromide to afford pyrrolo-pyrazinones with high efficiency under very mild conditions. The mechanism for the formation of the products is discussed and supported by DFT calculations. (C) 2014 Elsevier Ltd. ...
Synthesis of ferrocenyl pyrazoles by the reaction of (2-formyl-1-chlorovinyl)ferrocene with hydrazines
Zora, Metin (Elsevier BV, 2007-10-15)
Synthesis of ferrocenyl-substituted pyrazoles via the reaction between (2-formyl-1-chlorovinyl)ferrocene and hydrazine derivatives is described. Depending upon the substitution pattern of hydrazine, the reaction affords 1-alkyl/aryl-5-ferrocenylpyrazoles and/or 1-alkyl/ aryl-3-ferrocenylpyrazoles. The reaction appears to be general for a variety of hydrazine derivatives.
Synthesis of chiral lactones via the baeyer villiger oxidation of cyclic aromatic acetoxy ketones novel annulation reactions of 2-propynyl-1,3-dicarbonyl compounds to form pyrroles addition of acyl phosphonates to diethyl cyanophosphonate (depc)
Aybey, Asuman; Demir, Ayhan Sıtkı; Department of Chemistry (2009)
Chiral Baeyer-Villiger (BV) oxidation of cyclic ketones allows rapid access to asymmetric lactones as valuable intermediates in organic chemistry and frequently encountered precursors in enantioselective synthesis. In the first part, BV oxidation of functionalized ketones, especially cyclic -hydroxy and acetoxy ketones is described which could be a straightforward route to the -hydroxy lactones and -hydroxyalkanoic acid derivatives. The -acetoxylation of indanone, tetralone and chromanone derivatives by usi...
Synthesis of 1,2,3,5- tetrasubstituted pyrrole derivatives via 5-exo-dig type cyclization and stereoselective functionalisation of ferrocene derivatives
Kayalar, Metin; Demir, Ayhan Sıtkı; Department of Chemistry (2005)
A convenient and new method for the synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives starting from 1,3,-dicarbonyl compounds through acid catalyzed cyclization reaction is described. Alkylation of 1,3-dicarbonyl compound with propargyl bromide followed by one step cyclization with the introduction of primary amines in the presence of catalytic amount of triflouroacetic acid (TFA) affords the corresponding pyrrole derivatives in high yields. The investigations on the studies of developing a new meth...
Citation Formats
D. Baskin, Y. Cetinkaya, and M. Balcı, “Synthesis of dipyrrolo-diazepine derivatives via intramolecular alkyne cyclization,” TETRAHEDRON, pp. 4062–4070, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56372.