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 英文参考文献.docVIP

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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 英文参考文献.doc

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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 英文参考文献

Molecules 2000, 5, 1166-1174 molecules ISSN 1420-3049 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 Divi?ová, Helena Havli?ová, Petr Borek, and Pavel Pazdera* Department of Organic Chemistry, Faculty of Science, Masaryk University, CZ-611 37 Brno, Czech Republic. Tel.: +420 5 41129 305, Fax: +420 5 412 112 14. *Author to whom correspondence should be addressed; E-mail: pazdera@chemi.muni.cz Received:14 Aug 2000; in revised form 13 Sep 2000 / Accepted: 19 Sep 2000 / Published: 31 Oct 2000 Abstract: benzo[1,3]oxazolo[2,3-b]quinazolin-12-imine 12H-Benzo[1,3]oxazolo[2,3-b]quinazolin-12-imine (5a), 9-chloro-12H- (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-hydroxy- phenyl)-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 . Molecules 2000, 5 1167 Introduction In the search for economic and environmentally friendly synthetic methods, one-pot syntheses could offer a significant step ahead. N-(2-Cyanophenyl)chloromethanimidoyl chloride (1) [1] has been used al