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

doi:10.3390/51001166

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

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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

Hana Divišová, Helena Havlišová, Petr Borek and Pavel Pazdera*

Department of Organic Chemistry, Faculty of Science, Masaryk University, CZ-611 37 Brno, Czech Republic

* Author to whom correspondence should be addressed.

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

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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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