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Updated: May 17, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(2E)-2-[1-(2-Hy-droxy-4-meth-oxy-phenyl)ethyl-idene]-N-phenyl-hydrazine-carbox-amide monohydrate
C F Annie1, Jinsa Mary Jacob, M Sithambaresan
1Department of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India.
Abstract:
The title compound, C(16)H(17)N(3)O(3)·H(2)O, exists in the E conformation with respect to the azomethine C=N double bond. While the phenyl ring is almost coplanar with the central hydrazinecarboxamide group [dihedral angle = 14.18 (11)°], it is twisted slightly with respect to the other aromatic ring in the mol-ecule, with a dihedral angle of 22.88 (13)°. The packing is dominated by O-H⋯O, N-H⋯O and C-H⋯O hydrogen-bond inter-actions, forming a three-dimensional supra-molecular structure which is augmented by two types of C-H⋯π inter-actions. An intramolecular O-H⋯N interaction is also present in the molecule.
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The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
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Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

