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Molecules 2000, 5(10), 1166-1174; doi:10.3390/51001166
Article

One-pot Syntheses of Fused Quinazolines by Reaction of N-(2-Cyanophenyl)chloromethanimidoyl Chloride. I. A New Synthesis of 1,3-Oxazolo- and 1,3-Oxazino[2,3-b]quinazolines

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Received: 14 August 2000; in revised form: 13 September 2000 / Accepted: 19 September 2000 / Published: 31 October 2000
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Abstract: 12H-Benzo[1,3]oxazolo[2,3-b]quinazolin-12-imine (5a), 9-chloro-12Hbenzo[1,3]oxazolo[2,3-b]quinazolin-12-imine (5b), 2,3-dihydro-5H-[1,3]oxazolo[2,3-b]quinazolin-5-imine (5c), 2,3-dihydro-3,3-dimethyl-5H-[1,3]oxazolo[2,3-b]quinazolin-5-imine (5d) and 3,4--dihydro-2H,6H-[1,3]oxazino[2,3-b]quinazolin-6-imine (5e) were synthesized in a one-pot reaction of N-(2-cyanophenyl)chloromethanimidoyl chloride (1) with 2-aminophenols, 2-aminoethanol, and 3-aminopropanol in the presence of a base. The course of the reaction was controlled by the temperature and the amount of base used. N-(2-Cyanophenyl)-(2-hydroxyanilino)methanimidoyl chloride (3a), 2-chloro-3-(2-hydroxyphenyl)-3,4-dihydroquinazolin-4-imine (4a) and 6-imino-2H, 3H, 4H, 6H, 11H-1,3-oxazino[2,3-b]-5-quinazolinium chloride (6) were identified as intermediates of the one-pot process.
Keywords: N-(2-cyanophenyl)chloromethanimidoyl chloride; 1; 3-oxazolo[2; 3-b]- quinazoline; 1; 3-oxazino[2; 3-b]quinazoline; methanimidoyl chloride; fused quinazolines; one-pot synthesis N-(2-cyanophenyl)chloromethanimidoyl chloride; 1; 3-oxazolo[2; 3-b]- quinazoline; 1; 3-oxazino[2; 3-b]quinazoline; methanimidoyl chloride; fused quinazolines; one-pot synthesis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Divišová, H.; Havlišová, H.; Borek, P.; Pazdera, P. One-pot Syntheses of Fused Quinazolines by Reaction of N-(2-Cyanophenyl)chloromethanimidoyl Chloride. I. A New Synthesis of 1,3-Oxazolo- and 1,3-Oxazino[2,3-b]quinazolines. Molecules 2000, 5, 1166-1174.

AMA Style

Divišová H, Havlišová H, Borek P, Pazdera P. One-pot Syntheses of Fused Quinazolines by Reaction of N-(2-Cyanophenyl)chloromethanimidoyl Chloride. I. A New Synthesis of 1,3-Oxazolo- and 1,3-Oxazino[2,3-b]quinazolines. Molecules. 2000; 5(10):1166-1174.

Chicago/Turabian Style

Divišová, Hana; Havlišová, Helena; Borek, Petr; Pazdera, Pavel. 2000. "One-pot Syntheses of Fused Quinazolines by Reaction of N-(2-Cyanophenyl)chloromethanimidoyl Chloride. I. A New Synthesis of 1,3-Oxazolo- and 1,3-Oxazino[2,3-b]quinazolines." Molecules 5, no. 10: 1166-1174.


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