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

doi:10.3390/10091209

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

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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

M. Tulyasheva, B. Rasulev* , A. Tojiboev, K. Turgunov, B. Tashkhodjaev, N. Abdullaev and K Shakhidoyatov

Institute of the Chemistry of Plant Substances AS RUz, Uzbekistan

* Author to whom correspondence should be addressed.

Received: 10 June 2005; in revised form: 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 Р2_1/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.

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MDPI and ACS Style

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.

AMA Style

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(9):1209-1217.

Chicago/Turabian Style

Tulyasheva, M.; Rasulev, B.; Tojiboev, A.; Turgunov, K.; Tashkhodjaev, B.; Abdullaev, N.; Shakhidoyatov, K. 2005. "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 10, no. 9: 1209-1217.

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