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Pregled bibliografske jedinice broj: 871831

New aniline photocage for carboxylic acids


Škalamera, Đani; Blažek Bregović, Vesna; Basarić, Nikola
New aniline photocage for carboxylic acids // 25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem 3. simpozij "Vladimir Prelog" / Poreč, Hrvatska
Poreč, Hrvaska, 2017. (poster, međunarodna recenzija, sažetak, znanstveni)


Naslov
New aniline photocage for carboxylic acids

Autori
Škalamera, Đani ; Blažek Bregović, Vesna ; Basarić, Nikola

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem 3. simpozij "Vladimir Prelog" / Poreč, Hrvatska / - , 2017

Skup
25. HSKIKI

Mjesto i datum
Poreč, Hrvaska, 19-22.04.2017

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Anilines, photocage, photochemistry, protective groups

Sažetak
Photocleavable protecting groups (PPGs, photocages) are extensively used in chemical and biological sciences. It was shown that they can be used for light-controlled small molecule release (NO, H2S, CO, HNO) in biological systems [1], photocontrolled targeted drug delivery [2] and in molecular imaging and cell biology [3]. Very important area for application of PPGs is organic synthesis. Typical protecting groups used in organic synthesis (e.g. Boc, Fmoc) require some specific reagents/conditions for their removal. On the other hand, for removal of PPGs only iradiation is required (usually UV), which is big advantage in comparison with the standard protecting groups. Three main classes of PPGs described in the literature are based on: 2-nitrobenzyl, carbonyl or benzyl moieties.[4] However, these PPGs suffer from some limitations in their application, e. g. for 2-nitrobenzylalcohols the decaging reaction is slow. Therefore, research for new PPGs is very important topic of current research in organic photochemistry. Wang et al. have recently reported an interesting example of photocage for alcohols, based on m-hydroxyaniline ethers.[5] We decided to further develop this type of protecting group and expand their application for the protection of carboxylic acids. A systematic study of photochemical reactivity was conducted on o-, m- and p-substituted aniline-based PPGs. We have found out that a range of structurally different carboxylic acids can be easily converted to o-hydroxymehtylaniline esters ih high yield. The photodeprotection was accomplished under mild conditions (aqueous CH3CN), using 300 nm light. After the photodecageing, only aqueous workup (extraction) was required to obtain pure acid, without the need for the product chromatographic purification or crystallization. Furthermore, we have demonstrated that aniline alcohol can be regenerated from the photodeprotection reaction and reused.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

Napomena
Anilines, photocage, photochemistry, protective groups



POVEZANOST RADA


Projekt / tema
fotokemija anilinskih derivata u svrhu razvoja novih fotouklonjivih zaštitnih skupina
HRZZ-IP-2014-09-6312 - Supramolekulska kontrola fotokemijskih reakcija eliminacije (Nikola Basarić, )
Projekt HAZU - Sinteza

Ustanove
Institut "Ruđer Bošković", Zagreb,
Hrvatska akademija znanosti i umjetnosti