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Molecules 2005, 10(9), 1209-1217; doi:10.3390/10091209
Article

Synthesis, Tautomeric States and Crystal Structure of (Z)-Ethyl 2-Cyano-2-(3H-Quinazoline-4-ylidene) Acetate and (Z)-Ethyl 2-Cyano-2-(2-Methyl-3H-Quinazoline-4-ylidene) Acetate

,
* , , , ,  and
Institute of the Chemistry of Plant Substances AS RUz, Uzbekistan
* Author to whom correspondence should be addressed.
Received: 10 June 2005 / Revised: 29 June 2005 / Accepted: 30 June 2005 / Published: 30 September 2005
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Abstract

The new compounds (Z)-ethyl 2-cyano-2-(3H- and 2-methyl-3H-quinazoline-4-ylidene) acetate (1 and 2, respectively) were synthesized by multi-step reactions. Thestructures in a solution have been determined by 1H-NMR spectroscopy and in the crystalform by X-ray analysis. Molecule 1 crystallized in a primitive monoclinic cell, spacegroup Р21/c. The cell dimensions are a=7.970(6) å, b=7.061(2) å, c=20.537(7) å,β=97.69(5)°, V=1145.3(10) å3. Molecule 2 crystallized in a triclinic cell, space group P-1, the cell dimensions are a=8.196(5) å, b=8.997(6) å, c=9.435(4) å, α=74.22(4)°,β=89.75(4)°, γ=74.07(5)°, V=641.9(6) å3. In both compounds the presence of intra-molecular NH---O=C hydrogen bonding between the nitrogen atom in position 3 of thequinazoline ring and a carbonyl group of the ethyl cyanoacetate residue was proven byquantum-chemical, 1H-NMR and X-ray methods.
Keywords: Quinazolines; activated methylene groups; intramolecular hydrogen bonding; tautomery; quantum-chemical calculations. Quinazolines; activated methylene groups; intramolecular hydrogen bonding; tautomery; quantum-chemical calculations.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Tulyasheva, M.; Rasulev, B.; Tojiboev, A.; Turgunov, K.; Tashkhodjaev, B.; Abdullaev, N.; Shakhidoyatov, K. Synthesis, Tautomeric States and Crystal Structure of (Z)-Ethyl 2-Cyano-2-(3H-Quinazoline-4-ylidene) Acetate and (Z)-Ethyl 2-Cyano-2-(2-Methyl-3H-Quinazoline-4-ylidene) Acetate. Molecules 2005, 10, 1209-1217.

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