The novel spirooxindoline fused [1,3]oxazines were efficiently synthesized from Diels-Alder reaction of N-arylmaleimides with 1,2-dihydro-2-oxospiro[3H-indole-3,2＇-[2H,9aH-pyrido[2,1-b][l,3]oxazines], which were gene...The novel spirooxindoline fused [1,3]oxazines were efficiently synthesized from Diels-Alder reaction of N-arylmaleimides with 1,2-dihydro-2-oxospiro[3H-indole-3,2＇-[2H,9aH-pyrido[2,1-b][l,3]oxazines], which were generated in situ from three-component reactions of substituted pyridines and isatins with methyl propiolate, or di- methyl acetylenedicarboxylate. The stereochemistry of the products was clearly clarified by the analysis of 1H NMR data and single crystal structures of the obtained polycyclic compounds.展开更多
Halogenation of N-cinnamylbenzamides and N-[(2H-chromen-3-yl)methyl]benzamides using electrophilic halogen source was reported.Various halogenated dihydro-1,3-oxazine derivatives(45 examples)were synthesized in high t...Halogenation of N-cinnamylbenzamides and N-[(2H-chromen-3-yl)methyl]benzamides using electrophilic halogen source was reported.Various halogenated dihydro-1,3-oxazine derivatives(45 examples)were synthesized in high to excellent yields(up to 98%yields),as well as halogenated dihydrochromeno-1,3-oxazine derivatives(56 examples,up to 96%yields).The properties of mild conditions,metal-free and high efficiency of the reaction made it a promising strategy in future applications for the construction of carbon-halogen(fluorine,F;chlorine,Cl;bromine,Br;iodine,I)bond and 1,3-oxazine derivatives.展开更多
Synthesis of 3,3＇,4,4＇-tetrahydro-4,4＇-bibenzo[e][1,3]oxazine-2,2＇-diones via reaction of salicylidendphenylhy- drazone and triphosgene with the aid of low-valent titanium reagent is described. This method has the...Synthesis of 3,3＇,4,4＇-tetrahydro-4,4＇-bibenzo[e][1,3]oxazine-2,2＇-diones via reaction of salicylidendphenylhy- drazone and triphosgene with the aid of low-valent titanium reagent is described. This method has the advantages of accessible starting materials, good yields and short reaction time.展开更多
Herein, we report a novel synthesis of 1,3-oxazin-6-ones from enamides with CO2 through C--H carboxylation and one-pot cyclization. This transition-metal-free and redox-neutral process features broad substrate scope, ...Herein, we report a novel synthesis of 1,3-oxazin-6-ones from enamides with CO2 through C--H carboxylation and one-pot cyclization. This transition-metal-free and redox-neutral process features broad substrate scope, good functional group tolerance and facile product derivatization. The nucleophilic attack to CO2 from the electron-rich alkene is demonstrated for this reaction.展开更多
Flavonoids exhibit a wide range of biological activities including anti-inflammatory activity, while some 1,3-benzoxazine derivatives show anti-inflammatory activity. In order to explore the novel anti-inflammatory ag...Flavonoids exhibit a wide range of biological activities including anti-inflammatory activity, while some 1,3-benzoxazine derivatives show anti-inflammatory activity. In order to explore the novel anti-inflammatory agents, based on the principles of bioisosterism and hybridization, ten novel ehromeno[8,7-e][1,3]oxazin-4-ones were syn- thesized and characterized with IR, ^1H NMR, MS and elemental analyses. The anti-inflammatory activities of the target compounds were evaluated via the croton oil-induced ear oedema test in Swiss mice. According to screened resuits, some target compounds show potent anti-inflammatory activity.展开更多
A facile solid phase synthesis of 2-substituted 1,3-oxazin-6-ones using polymer-supported Meldrums acid has been reported. Reaction of the resin-bound cyclic malonic acid ester with triethyl orthoformate and subsequen...A facile solid phase synthesis of 2-substituted 1,3-oxazin-6-ones using polymer-supported Meldrums acid has been reported. Reaction of the resin-bound cyclic malonic acid ester with triethyl orthoformate and subsequent dou-ble substitution with amide, afforded the corresponding polymer-supported acylaminomethylene cyclic malonic acid ester, which upon thermal treatment led to 1, 3-oxazin-6-ones in good yields and with high purity.展开更多
A straiglitforward and efficient synthetic method of 2′-(dialkylammo)-l-alkyl-4′H-spiro[indoline-3,5′-oxazole]-2,4′-diones and 2-(dialkylamino)-5,6-dihydro-4H-naphtho[2,1-e][1,3]oxazin-4-one-derivatives have been ...A straiglitforward and efficient synthetic method of 2′-(dialkylammo)-l-alkyl-4′H-spiro[indoline-3,5′-oxazole]-2,4′-diones and 2-(dialkylamino)-5,6-dihydro-4H-naphtho[2,1-e][1,3]oxazin-4-one-derivatives have been developed from a-hydroxy andβ-carbonyl amides and various Vilsmeier salts.A wide range of heterocyclic compounds were obtained in excellent yields(up to 97%),which will provide promising candidates lor chemical biology and drug discovery.展开更多
基金This work was financially supported by the National Natural Science Foundation of China （Grant No. 21272200） and the Priority Academic Program Development of Jiangsu Higher Education Institutions. We would also like to express our sincere thanks to the Analysis Center of Yangzhou University for providing all necessary instruments for characterization of structures.
文摘The novel spirooxindoline fused [1,3]oxazines were efficiently synthesized from Diels-Alder reaction of N-arylmaleimides with 1,2-dihydro-2-oxospiro[3H-indole-3,2＇-[2H,9aH-pyrido[2,1-b][l,3]oxazines], which were generated in situ from three-component reactions of substituted pyridines and isatins with methyl propiolate, or di- methyl acetylenedicarboxylate. The stereochemistry of the products was clearly clarified by the analysis of 1H NMR data and single crystal structures of the obtained polycyclic compounds.
基金supported by the National Natural Science Foundation of China(No.22108264).
文摘Halogenation of N-cinnamylbenzamides and N-[(2H-chromen-3-yl)methyl]benzamides using electrophilic halogen source was reported.Various halogenated dihydro-1,3-oxazine derivatives(45 examples)were synthesized in high to excellent yields(up to 98%yields),as well as halogenated dihydrochromeno-1,3-oxazine derivatives(56 examples,up to 96%yields).The properties of mild conditions,metal-free and high efficiency of the reaction made it a promising strategy in future applications for the construction of carbon-halogen(fluorine,F;chlorine,Cl;bromine,Br;iodine,I)bond and 1,3-oxazine derivatives.
基金Project supported by the National Natural Science Foundation of China （No. 21072144） and the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions （No. 10KJAI50049）.
文摘Synthesis of 3,3＇,4,4＇-tetrahydro-4,4＇-bibenzo[e][1,3]oxazine-2,2＇-diones via reaction of salicylidendphenylhy- drazone and triphosgene with the aid of low-valent titanium reagent is described. This method has the advantages of accessible starting materials, good yields and short reaction time.
文摘Herein, we report a novel synthesis of 1,3-oxazin-6-ones from enamides with CO2 through C--H carboxylation and one-pot cyclization. This transition-metal-free and redox-neutral process features broad substrate scope, good functional group tolerance and facile product derivatization. The nucleophilic attack to CO2 from the electron-rich alkene is demonstrated for this reaction.
基金Supported by the National Natural Science Foundation of China(No.40724053)
文摘Flavonoids exhibit a wide range of biological activities including anti-inflammatory activity, while some 1,3-benzoxazine derivatives show anti-inflammatory activity. In order to explore the novel anti-inflammatory agents, based on the principles of bioisosterism and hybridization, ten novel ehromeno[8,7-e][1,3]oxazin-4-ones were syn- thesized and characterized with IR, ^1H NMR, MS and elemental analyses. The anti-inflammatory activities of the target compounds were evaluated via the croton oil-induced ear oedema test in Swiss mice. According to screened resuits, some target compounds show potent anti-inflammatory activity.
基金Project supported by the National Natural Science Foundation of China (No. 20072032).
文摘A facile solid phase synthesis of 2-substituted 1,3-oxazin-6-ones using polymer-supported Meldrums acid has been reported. Reaction of the resin-bound cyclic malonic acid ester with triethyl orthoformate and subsequent dou-ble substitution with amide, afforded the corresponding polymer-supported acylaminomethylene cyclic malonic acid ester, which upon thermal treatment led to 1, 3-oxazin-6-ones in good yields and with high purity.
基金the National Natural Science Foundation of China(No.51373067).
文摘A straiglitforward and efficient synthetic method of 2′-(dialkylammo)-l-alkyl-4′H-spiro[indoline-3,5′-oxazole]-2,4′-diones and 2-(dialkylamino)-5,6-dihydro-4H-naphtho[2,1-e][1,3]oxazin-4-one-derivatives have been developed from a-hydroxy andβ-carbonyl amides and various Vilsmeier salts.A wide range of heterocyclic compounds were obtained in excellent yields(up to 97%),which will provide promising candidates lor chemical biology and drug discovery.
