Photoreactions of 4- and 3-Azidocoumarins in the Presence of Nucleophiles

K, Ito; Higuchi, Y.; Tame, Chika; Hariya, Junko

doi:10.3987/com-92-s(t)88

Cited by 19 publications

(4 citation statements)

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“…From Halocoumarins and Analogues are important building blocks for the synthesis of flurophores [141,242]. Several aminocoumarins were obtained by photoreactions of 4-and 3-azidocoumarins, in the presence of different types of nucleophiles [243].…”

Section: From Arylcoumarinsmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

885

458

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Coumarins, also known as benzopyrones, are present in remarkable amounts in plants, although their presence has also been detected in microorganisms and animal sources. The structural diversity found in this family of compounds led to the division into different categories, from simple coumarins to many other kinds of policyclic coumarins, such as furocoumarins and pyranocoumarins. Simple coumarins and analogues are a large class of compounds that have attracted their interest for a long time due to their biological activities: they have shown to be useful as antitumoural, anti-HIV agents and as CNS-active compounds. Furthermore, they have been reported to have multiple biological activities (anticoagulant, anti-inflammatory), although all these properties have not been evaluated systematically. In addition, their enzyme inhibition properties, antimicrobial and antioxidant activities are other foremost topics of this field of research. The present work is to survey the information published or abstracted from 1990 till 2003, which is mainly related to the occurrence, synthesis and biological importance of simple coumarins and some analogues, such as biscoumarins and triscoumarins. Data are also highlighted, concerning the development of new synthetic strategies that could help in drug design and in the work on SAR or QSAR.

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Section: From Arylcoumarinsmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

885

458

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show abstract

“…Similarly, the reaction of 4-azidocoumarins with nitrogen nucleophiles affected -pyrone ring fission (15) . Thus, the reaction of 4-chloro-3-formyl coumarin (XII a-c ) with sodium azide in DMF afforded the corresponding 4-azido-3-formyl-1-benzopyran-2-one (XIII).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 4-Hydroxy-3-Substituted Coumarins of Expected Biological Activity and Their Reactions With Some Nucleophiles

El-Ghaffar

Dawood

El-Salam

et al. 2008

Al-Azhar Bulletin of Science

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Abstract3-Acetyl-4-hydroxy substituted coumarins (II a-c ) were prepared. Their reactions with hydrazines in DMF gave the corresponding 4-hydroxy -(3-substituted pyrazolin-3-yl)coumarins (IV a-f ) via the intermediate hydrazone (III). Their reaction with hydroxylamine hydrochloride gave the corresponding isoxazol-3-yl coumarin (VI a-c ) and (VII a,b ) via the oxime intermediate (V). Reaction of II with aromatic aldehydes gave the corresponding chalcone derivatives (VIII a-k ) which were reacted with hydrazines and hydroxyl amine hydrochloride and gave (IX a ) and (X a-c ). Condensation of (II a-c ) with aromatic aldehydes, malononitrile in the presence ammonium acetate yielded the corresponding 3-cyano-4-aryl nictoinamido-6-ylcoumarin (XI a-f ). 4-Hydroxy comumarin(1 a-c ) on treatment with POCl 3 in DMF give the corresponding 4-Chloro-3-formyl coumarin (XII a-c ) which on treatment with sod azide gave the corresponding 4-azido-3-formyl coumarin (XIII a-c ). 4-chloro-3-formyl coumarine (XII )on treatment with hydrazine gave pyrazolo coumarin derivatives (XIV a-d ) and on treatment with hydroxylamine hydrochloride gave 4-chloro-3-aldo oxime coumarin derivatives (XV a,b ). On treatment of 4-azido-3-formyl coumarin with active methylene compounds such as malononitrile and ethyl cyanocetate derivatives gave (XVI a-d ) respectively.The antibacterial and antifungal activities of some compounds have been described.

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“…The lowest triazole yield (6-8%) was observed for 3-azidocoumarine 2d, which has been reported to be photolabile. 43 For the other azides 2a-c and 2f-h, triazole yields were 11-39%. Further irradiation did not increase the conversion, which may indicate the role of selenium as an internal filter (see above) and potential side photoreactions of the azides reported in the literature.…”

mentioning

confidence: 96%

“…Surprisingly, the triazole yields were similar or lower compared to those previously determined. The only exception was the reaction of azide 2d (the most photoactive azide 43 ), where the post-irradiation addition of this azide prevented its photodecomposition and the total yield of triazole increased. In all cases, the starting cycloocta-1,2,3-selenadiazole 1 always remained in the reaction mixture.…”

mentioning

confidence: 99%

Study and application of noncatalyzed photoinduced conjugation of azides and cycloocta-1,2,3-selenadiazoles

et al. 2016

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The non-catalyzed cycloaddition of eight structurally different azides with cyclooctyne generated in situ by the photolysis of cycloocta-1,2,3-selenadiazole gives 1,2,3-triazole derivatives as the main products. The application of this reaction was demonstrated by the photoconjugation reaction of cycloocta-1,2,3-selenadiazole with an avidin-modified biotin complex to introduce a new strategy in the non-catalyzed synthesis of bioconjugates.

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Photoreactions of 4- and 3-Azidocoumarins in the Presence of Nucleophiles

Cited by 19 publications

References 0 publications

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Synthesis of 4-Hydroxy-3-Substituted Coumarins of Expected Biological Activity and Their Reactions With Some Nucleophiles

Study and application of noncatalyzed photoinduced conjugation of azides and cycloocta-1,2,3-selenadiazoles

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