Flavin-Mediated Visible-Light [2+2] Photocycloaddition of Nitrogen- and Sulfur-Containing Dienes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F17%3A43914935" target="_blank" >RIV/60461373:22310/17:43914935 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22810/17:43914935

Výsledek na webu

<a href="http://dx.doi.org/10.1002/ejoc.201601377" target="_blank" >http://dx.doi.org/10.1002/ejoc.201601377</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.201601377" target="_blank" >10.1002/ejoc.201601377</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Flavin-Mediated Visible-Light [2+2] Photocycloaddition of Nitrogen- and Sulfur-Containing Dienes

Popis výsledku v původním jazyce

The [2+2] photocycloaddition mediated by 1-butyl-3-methyl-7,8-dimethoxyalloxazine (1) has been found to be an effective tool for cyclising omega-phenyl- and omega,omega&apos;-diphenyl-4-aza-1,6-heptadienes, in which the nitrogen atom is protected by acylation or quaternisation, towards the synthesis of a variety of phenyl- and diphenyl-3-azabicyclo[3.2.0]heptanes and their corresponding quaternary salts. Thia derivatives, with the sulfur atom in the form of a sulfone group, underwent an analogous cyclisation. Advantageously, visible light (400 nm) was used for the cycloadditions in the presence of 1, in contrast to the previously described procedures affording azabicyclo[3.2.0]heptanes by using UV irradiation. Practical applications are demonstrated through the synthesis of bicyclic quaternary ammonium salts, 6-phenyl-azabicyclo[3.2.0]heptanesknown to exhibit biological activity or chiral spiro ammonium salts. Flavin 1 was also found to promote the efficient E -&gt; Z isomerisation of electron-rich cinnamyl derivatives to produce mixtures enriched with the Z isomer (with Z/E ratios of up to 77:23).

Název v anglickém jazyce

Flavin-Mediated Visible-Light [2+2] Photocycloaddition of Nitrogen- and Sulfur-Containing Dienes

Popis výsledku anglicky

The [2+2] photocycloaddition mediated by 1-butyl-3-methyl-7,8-dimethoxyalloxazine (1) has been found to be an effective tool for cyclising omega-phenyl- and omega,omega&apos;-diphenyl-4-aza-1,6-heptadienes, in which the nitrogen atom is protected by acylation or quaternisation, towards the synthesis of a variety of phenyl- and diphenyl-3-azabicyclo[3.2.0]heptanes and their corresponding quaternary salts. Thia derivatives, with the sulfur atom in the form of a sulfone group, underwent an analogous cyclisation. Advantageously, visible light (400 nm) was used for the cycloadditions in the presence of 1, in contrast to the previously described procedures affording azabicyclo[3.2.0]heptanes by using UV irradiation. Practical applications are demonstrated through the synthesis of bicyclic quaternary ammonium salts, 6-phenyl-azabicyclo[3.2.0]heptanesknown to exhibit biological activity or chiral spiro ammonium salts. Flavin 1 was also found to promote the efficient E -&gt; Z isomerisation of electron-rich cinnamyl derivatives to produce mixtures enriched with the Z isomer (with Z/E ratios of up to 77:23).

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA14-09190S" target="_blank" >GA14-09190S: Fotoorganokatalytická metateze: [2+2] cykloadice alkenů a štěpení cyklobutanového kruhu s využitím flavinů a viditelného světla</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2017

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Svazek periodika

2017

Číslo periodika v rámci svazku

15

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

8

Strana od-do

2139-2146

Kód UT WoS článku

000399701800018

EID výsledku v databázi Scopus

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