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1 article(s) from Minyaev, Mikhail E

Synthesis of substituted 8H-benzo[h]pyrano[2,3-f]quinazolin-8-ones via photochemical 6π-electrocyclization of pyrimidines containing an allomaltol fragment

Constantine V. Milyutin,
Andrey N. Komogortsev,
Boris V. Lichitsky,
Mikhail E. Minyaev and
Valeriya G. Melekhina

Beilstein J. Org. Chem. 2023, 19, 778–788, doi:10.3762/bjoc.19.58

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Scheme 1: Photochemical behavior of terarylenes containing an allomaltol fragment.

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Scheme 2: Synthesis of starting compounds 9. Reaction conditions: 13 (1 mmol), NH₂CN (14, 3 mmol, 0.13 g), Et...

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Scheme 3: Proposed mechanism for the formation of compounds 9.

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Scheme 4: Synthesis of methylated derivatives 10. Reaction conditions: 9 (1 mmol), MeI (3 mmol, 0.43 g), K₂CO₃...

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Figure 1: ¹H NMR monitoring of the photoreaction of compound 10a under UV irradiation (365 nm) in DMSO-d₆ sol...

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Figure 2: The crystal structure of compound 11a (one of two polymorph modifications; p = 50%), CCDC 2248033.

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Scheme 5: Photochemical synthesis of compounds 11 and 12.

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Scheme 6: Proposed mechanism for the studied photoreaction.

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Scheme 7: Synthesis of compounds 11g–j starting from pyrimidines 9. Reaction conditions: 9 (0.5 mmol), DMF (1...

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Figure 3: One of crystallographically unique molecules of 11g (p = 50%), CCDC 2248035.

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Scheme 8: Synthesis of photoproducts 12. Reaction conditions: method A) 10 (0.5 mmol), DMF (15 mL) irradiatio...

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Published 07 Jun 2023

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