CRYSTAL STRUCTURE OF 2-[BENZYL-(7-OXO-CYCLOHEPTA-1,3,5-TRIENYL)-AMINO]-N-CYCLOHEXYLPROPANAMIDE

Single crystal X-ray structure Smiles rearrangement Ugi-type coupling tropolone cyclohexylisocyanide benzyl amine acetaldehyde Ugi—Smiles-type reaction.

СИНТЕЗ И СТРУКТУРА ИНГИБИТОРА КОРРОЗИИ — ТЕТРАНАТРИЙ НИТРИЛОТРИСМЕТИЛЕНФОСФОНАТОЦИНКАТА ТРИДЕКАГИДРАТА Na4[ZnN(CH2PO3)3]⋅13H2O, ЛОКАЛЬНОЕ АТОМНОЕ СТРОЕНИЕ КОМПЛЕКСОВ МЕДИ С 2-ТОЗИЛАМИНОБЕНЗАЛЬ-2′-АМИНО-5′-ХЛОРТИОФЕНОЛОМ, ...

Том 56, 3 UDC 548.737:541.67 2-[BENZYL-(7-OXO-CYCLOHEPTA-1,3,5-TRIENYL)-AMINO]-N-CYCLOHEXYLPROPANAMIDE CRYSTAL STRUCTURE OF A. Ramazani1, S.W. Joo2, I. Amini3, K. Ślepokura4, T. Lis4, A. Souldozi5 1Department of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran 2 E-mail: aliramazani@gmail.com School of Mechanical Engineering, Yeungnam University, Republic of Korea 3 E-mail: swjoo@yu.ac.kr 4Department of Chemistry, Payame Noor University, Tehran, Iran 5Faculty of Chemistry, University of Wrocław, Wrocław, Poland Department of Chemistry, Urmia Branch, Islamic Azad University, Urmia, Iran Received October 05, 2013 The title compound 2-[benzyl-(7-oxo-cyclohepta-1,3,5-trienyl)-amino]-N-cyclohexylpropanemide is synthesized and studied by the single crystal X-ray diffraction method. <...> The structure of the product was confirmed by IR, 1H and 13C NMR spectroscopy, and mass spectrometry. <...> The tropone oxygen atom plays an important role in the solid-state molecular structure stabilization by being involved in intramolecular N—H O and C—H O contacts. <...> DOI: 10.15372/JSC20150310 Keywords: Single crystal X-ray structure, Smiles rearrangement, Ugi-type coupling, tropolone, cyclohexylisocyanide, benzyl amine, acetaldehyde, Ugi—Smiles-type reaction. <...> The special features of isocyanide-based multi-component reactions (abbreviated to IMCRs by Ugi and Dцmling) such as the unique synthetic potential, convergent nature, high atom economy, ease of implementation, and the generation of molecular diversity are considered as acceptable factors in the relative efficiency of the reactions [ 1—6]. <...> In connection with our recent interest in isocyanide chemistry [ 7—9], we report the synthesis and structure of 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivative, i.e. 2-[benzyl-(7-oxo-cyclohepta-1,3,5-trienyl)-amino]-N-cyclohexylpropanamide, from the Ugi—Smiles-type reaction between acetaldehyde, benzylamine, cyclohexylisocyanide and tropolone. <...> According to our knowledge, solid-state structural data have not as yet been reported for compounds with the 2-(7-oxo-cyclohepta-1,3,5-trienylamino)-acetamide fragment [ 10 ]. <...> The methods used to follow the reactions were TLC and NMR. <...> TLC and NMR indicated that there was no side products. <...> Mass spectra were recorded on a FINNIGANMATT 8430 mass spectrometer operating at an ionization potential of 70 eV. Preparative thin layer chromatography was <...>

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