Methyl 2-benzamido-4-(3,4-dimethoxyphenyl)-5-methylbenzoate and N-{5-benzoyl-2-[(Z)-2-methoxyethenyl]-4-methylphenyl}benzamide

作者：Kranjc Kristof; Kocevar Marijan; Perdih Franc^*

来源：Acta Crystallographica Section C-Crystal Structure Communications, 2011, 67: O201-O205.

DOI：10.1107/S0108270111015794

Methyl 2-benzamido-4-(3,4-dimethoxyphenyl)-5-methylbenzoate, C24H23NO5, (Ia), and N-{5-benzoyl-2-[(Z)-2-methoxyethenyl]-4-methylphenyl}benzamide, C24H21NO3, (IIa), were formed via a Diels-Alder reaction of appropriately substituted 2H-pyran-2-ones and methyl propiolate or (Z)-1-methoxybut-1-en-3-yne, respectively. Each of these cycloadditions might yield two different regioisomers, but just one was obtained in each case. In (Ia), an intramolecular N-H center dot center dot center dot O hydrogen bond closes a six-membered ring. A chain is formed due to aromatic pi-pi interactions, and a three-dimensional framework structure is formed by a combination of C-H center dot center dot center dot O and C-H center dot center dot center dot pi(arene) hydrogen bonds. Compound (IIa) was formed not only regioselectively but also chemoselectively, with just the triple bond reacting and the double bond remaining unchanged. Compound (IIa) crystallizes as N-H center dot center dot center dot O hydrogen-bonded dimers stabilized by aromatic pi-pi interactions. Dimers of (IIa) are connected into a chain by weak C-H center dot center dot center dot pi(arene) interactions.

• 出版日期2011-6