Photoinduced Molecular Transformations. Part 142. One‐step syntheses of 1H‐benz[f]indole‐4,9‐diones and 1H‐indole‐4,7‐diones by a new regioselective photoaddition of 2‐amino‐1,4‐naphthoquinones and 2‐amino‐1,4‐benzoquinones with alkenes

doi:10.1002/HLCA.19930760818

Paper

Photoinduced Molecular Transformations. Part 142. One‐step syntheses of 1H‐benz[f]indole‐4,9‐diones and 1H‐indole‐4,7‐diones by a new regioselective photoaddition of 2‐amino‐1,4‐naphthoquinones and 2‐amino‐1,4‐benzoquinones with alkenes

Published Dec 15, 1993 · Kazuhiro Kobayashi, H. Takeuchi, S. Seko

Helvetica Chimica Acta

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14

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Abstract

The 2,3-dihydro-1H-benz[f]indole-4,9-diones 3a–d, h were formed in a one-step reaction in 13–82% yield by an unprecedented [3 + 2] regioselective photoaddition of 2-amino-1,4-naphthoquinone (1) with various electronrich alkenes 2 (Scheme 1, Table). The [3 + 2] photoadducts derived from 1 with vinyl ethers and vinyl acetate gave 1H-benz[f]indole-4,9-diones 4e, f, i, in 33–72% yield, by spontaneous loss of the corresponding alcohol or AcOH from the resulting adducts; 4i has a kinamycin skeleton. The [3 + 2] photoaddition also took place on irradiation of the differently substituted amino-1,4-benzoquinones 6, 7, and 12 and excess alkenes 2 in benzene, giving 1H-indole-4,7-dione derivatives 13 and 14 (Scheme 3), 15a and 16 (Scheme 4), and 18 (Scheme 4), respectively. The initial products in these photoadditions were proved to be hydroquinones, the air oxidation of which yielded the heterocyclic quinones; 2,3-dihydro-2-methoxy-2-methyl-5-phenyl-1H-indole-1,4,7-triyl triacetate (19) was isolated after treatment of the crude photoaddition mixture obtained from 2-amino-5-phenyl-1,4-benzoquinone (7) and 2-methoxyprop-1-ene (2f) with Ac2O and pyridine under N2. A pathway leading to the annelated hydroquinones involving ionic intermediates arising from an electron transfer in these photoadditions is proposed (Scheme 5).

Study Snapshot

This study demonstrates a new regioselective photoaddition method for synthesis of 1H-benz[f]indole-4,9-diones and 1H-indole-4,7-diones in one-step reactions, with potential applications in organic

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Photoinduced Molecular Transformations. Part 142. One‐step syntheses of 1H‐benz[f]indole‐4,9‐diones and 1H‐indole‐4,7‐diones by a new regioselective photoaddition of 2‐amino‐1,4‐naphthoquinones and 2‐amino‐1,4‐benzoquinones with alkenes

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References

Photoinduced molecular transformations. 140. New one-step general synthesis of naphtho[2,3-b]furan-4,9-diones and their 2,3-dihydro derivatives by the regioselective [3 + 2] photoaddition of 2-hydroxy-1,4-naphthoquinones with various alkynes and alkenes: application of the photoaddition to a two-ste

Photoaddition of 2-hydroxy-1,4-naphthoquinones to various alkenes in acetone leads to the formation of 2,3-dihydronaphtho[2,3-b]furan-4,9-diones, which can be transformed into naph

Photo-induced molecular transformations. Part 123. One-step synthesis of 1H-benz[f]indole-4,9-diones by a new regioselective photoaddition of 2-amino-1,4-naphthoquinone with various alkenes and its application to one-step synthesis of kinamycin skeleton†‡

This study presents a new regioselective photoaddition method for synthesis of 1H-benz[f]indole-4,9-diones and their applications in the synthesis of kinamycin skeletons in one-step.

Photoinduced molecular transformations. Part 120. New one-step general synthesis of 2,3-dihydronaphtho[2,3-b]-furan-4,9-diones by regioselective photoaddition of 2-hydroxy-1,4-naphthoquinones with various alkenes and its application to a two-step synthesis of maturinone

This one-step synthesis allows for the two-step synthesis of maturinone, a natural quinone with a molecular weight of 68 kDa.

An Efficient Synthesis of 5,7-Dihydroxy-4-methylisobenzofuran-1(3N)-one, a Metabolite of aspergillus flavus and a Key Intermediate in the Synthesis of Mycophenolic Acid

This study presents an efficient new synthesis of 5,7-dihydroxy-4-methylisobenzofuran-1(3H)-one, a key intermediate in the synthesis of mycophenolic acid, using 1,2-dihydro-4,6-dimethoxy-3-methylbenzocyclobut

Synthesis of 4,7-indolequinones by photoinduced reaction of azidoquinones.

Photoinduced reaction of azidoquinones leads to the synthesis of 4,7-indolequinones, a model for mitomycin analogs, in moderate yield.

Photocycloaddition reaction of alkyl-substituted 1,4-naphthoquinones with olefins. Substituent effects on controlling the orientation of cycloaddition reaction.

The orientation of photocycloaddition reactions between alkyl-substituted 1,4-naphthoquinones and olefins is primarily influenced by van der Waals repulsion between the substituents of the quinone and olefin.

Citations

Synthesis, in vitro and in silico studies of indolequinone derivatives against clinically relevant bacterial pathogens.

The highly substituted indolequinones show promising antimicrobial properties against various bacteria, including MRSA, with potential for oral bioavailability and low toxicity.

Accessing benzo[f]indole-4,9-diones via a ring expansion strategy: silver-catalyzed tandem reaction of tosylmethyl isocyanide (TosMIC) with 2-methyleneindene-1,3-diones

Silver-catalyzed tandem reaction of TosMIC with 2-methyleneindene-1,3-diones allows for the direct synthesis of benzo[f]indole-4,9-diones through a domino [3+2]-cycloaddition/imi

Mn(II)-catalyzed synthesis of benzo[f]indole-4,9-diones via vinyl azides and 2-hydroxynaphthoquinone

Mn(II) acetate-catalyzed synthesis of benzo[f]indole-4,9-diones from vinyl azides and 2-hydroxynaphthoquinone provides a convenient and economical method for preparing polyfunctionalized benzo[f]in

Copper(II)-catalyzed sequential C,N-difunctionalization of 1,4-naphthoquinone for the synthesis of benzo[f]indole-4,9-diones under base-free condition.

Copper(II)-catalyzed sequential C,N-difunctionalization of 1,4-naphthoquinone with -enaminones efficiently synthesizes benzo[f]indole-4,9-diones under base-free conditions,

Chirogenic [3 + 2]-photocycloaddition reactions of 2-substituted naphthoquinones with cyclic alkenes

Chirogenic [3 + 2]-photocycloaddition reactions of 2-substituted naphthoquinones with cyclic alkenes can be enantioselective at low temperatures in nonpolar solvents, but enantiomeric excess remains low.