Abstract
The title compound, C31H34N2O9, is a product of the Michael addition of the cyclic secondary amine subunit of the (bispidino)aza-14-crown-4 ether to dimethyl acetylenedicarboxylate. The molecule comprises a tricyclic system containing the aza-14-crown-3 ether macrocycle and two six-membered piperidinone rings. The aza-14-crown-3-ether ring adopts a bowl conformation with a dihedral angle between the planes of the fused benzene rings of 51.14 (5)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The dimethyl ethylenedicarboxylate fragment has a cis configuration with a dihedral angle of 56.56 (7)° between the two carboxylate groups. The crystal packing is stabilized by weak C—H⋯O hydrogen bonds.
Highlights
In attempts to develop the chemistry for new azacrown systems and to obtain macrocyclic ligands bringing the desirable functional groups, we studied the Michael addition of the cyclic secondary amine subunit of theaza-14crown-4 ether to dimethyl acetylenedicarboxylate
We have found that the expected N-vynilation reaction of theazacrown ether proceeded smoothly to give an N-maleinate derivative of the azacrown system with a good yield (Fig. 1)
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x−1, y, z; (iii) x, −y+1/2, z−1/2
Summary
Truong Hong Hieu,a* Le Tuan Anh,a Anatoly T. Khrustalevc a Department of Chemistry, Vietnam National University, 144 Xuan Thuy, Cau Giay, Hanoi, Vietnam, bOrganic Chemistry Department, Russian People’s Friendship. University, Miklukho-Maklaya Street 6, Moscow, 117198, Russian Federation, and c. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B-334, Moscow 119991, Russian. R factor = 0.045; wR factor = 0.111; data-to-parameter ratio = 22.0
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