Synthesis, characterization, crystal and molecular structure of 1,5-Dihydro-2H-cyclopenta[1,2-b : 5,4-b ']dipyridin-2-imine

Date

2007-01-01

Author

Baysal, Akin
Durap, Feyyaz
Gumgum, Bahattin
Yildirim, Leyla T.
Ulku, Dincer
Boga, Ayse Dilek
Özkar, Saim

Metadata

Show full item record

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

Item Usage Stats

155
views

0
downloads

The reaction of 1,5-diliydro-2H-cyclopenta[1,2-b:5,4-b'ldipyridin-2-one (3) with an alkylamine (butvlamine, hexylamine or ethylenediamine) yields, quite unexpectedly and in the absence of catalyst, the novel compound 1,5-dihydro-2H-cyclopentafl,2-b:5.4-b']dipyridin-2-imine (4) as the sole, analytically pure, solid product, which was fully characterized. The structure of 4 was unequivocally solved by single-crystal X-ray-diffraction analysis. The compound crystallizes in a monoclinic cell (space group P 2(1/c)). with two molecules in the asymmetric unit. held together by intermolecular H-bonds. Compound 4 could be interesting as a bi- or even tridentate ligand, and exhibits a strong fluorescence upon excitation at 310 nm. A mechanism, based on the observed C-N bond cleavage, is proposed.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis

URI

https://hdl.handle.net/11511/44016

Journal

HELVETICA CHIMICA ACTA

DOI

https://doi.org/10.1002/hlca.200790120

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis and properties of a novel redox driven chemiluminescent material built on a terthienyl system Atilgan, Nurdan; Algi, Fatih; Önal, Ahmet Muhtar; CİHANER, ATİLLA (Elsevier BV, 2009-07-18) A novel redox driven chemiluminescent material built on a terthienyl system, namely 5,7-di-ethylenedioxythiophen-2-yl-2,3-dihydro-thieno[3,4-d]pyridazine-1,4-dione (ETE-Lum), which is soluble in both organic media and basic aqueous solution was synthesized and characterized. Furthermore, its polymer, PETE-Lum, which is one of the most rare examples of chemiluminescent polymeric materials bearing a pyridazine unit, was obtained successfully by electrochemical means. Both of the materials give chemiluminescen...
Chemistry of the benzotropone endoperoxides and their conversion into tropolone derivatives: Unusual endoperoxide rearrangements Guney, M; Dastan, A; Balcı, Metin (Wiley, 2005-01-01) The chemistry of two bicyclic endoperoxides, obtained by photooxygenation of 2,3-benzotropone (= 5H-benzocyclohepten-5-one 5) and of its ethyl carboxylate derivative 15, was investigated with the aim of synthesizing the respective benzotropolone derivatives. The reaction of the endoperoxide 10 derived from 5 with thiourea gave the desired benzotropolone, i.e., 6-hvdroxy-5H-benzocyclohepten-5-one (11), in high yield (Scheme 1). On the other hand, the endoperoxide 16 derived from the ethyl carboxylate derivat...
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.
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 and structural characterization of a novel seven-coordinate cobalt(II) complex: 2,9-Bis(ethanolamine)-1,10-phenanthrolinechlorocobalt(II) chloride BAYSAL, AKIN; AYDEMİR, MURAT; DURAP, FEYYAZ; Özkar, Saim; Yildirim, Leyla Tatar (Elsevier BV, 2011-05-31) Condensation reaction of 2,9-dicarboxaldehyde-1,10-phenanthroline with 2-aminoethanol followed by NaBH4 reduction yielded the polydentate Schiff base ligand 2,9-bis(ethanolamine)-1,10-phenanthroline in its reduced form. This ligand was characterized by elemental analysis, LC-MS, IR, UV-Vis and NMR spectroscopy. Reaction of the reduced Schiff base ligand with aqueous solution of cobalt(II) chloride affords 2,9-bis(ethanolamine)-1,10-phenanthrolinechlorocobalt(II) chloride in high yield. Single crystals of th...

Citation Formats

A. Baysal et al., “Synthesis, characterization, crystal and molecular structure of 1,5-Dihydro-2H-cyclopenta[1,2-b : 5,4-b ’]dipyridin-2-imine,” HELVETICA CHIMICA ACTA, pp. 1211–1217, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/44016.