Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives : An Energy-Efficient Approach
We report here an energy-efficient and straight synthesis of two new classes of derivatized fluorescent azatetracycles under ultrasound (US) irradiation. A first class of azatetracyclic compounds was synthesized by heterogeneous catalytic bromination of the α-keto substituent attached to the pyrrole moiety of the tetracyclic cycloadducts, while for the second, one class was synthesized by nucleophilic substitution of the bromide with the azide group. Comparative with conventional thermal heating (TH) under US irradiation, both types of reactions occur with substantially higher yields, shortened reaction time (from days to hours), lesser energy consumed, easier workup of the reaction, and smaller amounts of solvent required (at least three to five-fold less compared to TH), which make these reactions to be considered as energy efficient. The derivatized azatetracycle are blue emitters with λmax of fluorescence around 430-445 nm. A certain influence of the azatetracycle substituents concerning absorption and fluorescent properties was observed. Compounds anchored with a bulky azide group have shown decreased fluorescence intensity compared with corresponding bromides.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2022 |
|---|---|
| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:27 |
|---|---|
| Enthalten in: |
Molecules (Basel, Switzerland) - 27(2022), 10 vom: 16. Mai |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Zbancioc, Gheorghita [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
Azatetracyclic |
|---|
| Anmerkungen: |
Date Completed 31.05.2022 Date Revised 16.07.2022 published: Electronic Citation Status MEDLINE |
|---|
| doi: |
10.3390/molecules27103180 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM341529370 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM341529370 | ||
| 003 | DE-627 | ||
| 005 | 20231226012004.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231226s2022 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.3390/molecules27103180 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1138.xml |
| 035 | |a (DE-627)NLM341529370 | ||
| 035 | |a (NLM)35630657 | ||
| 035 | |a (PII)3180 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Zbancioc, Gheorghita |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives |b An Energy-Efficient Approach |
| 264 | 1 | |c 2022 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 31.05.2022 | ||
| 500 | |a Date Revised 16.07.2022 | ||
| 500 | |a published: Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a We report here an energy-efficient and straight synthesis of two new classes of derivatized fluorescent azatetracycles under ultrasound (US) irradiation. A first class of azatetracyclic compounds was synthesized by heterogeneous catalytic bromination of the α-keto substituent attached to the pyrrole moiety of the tetracyclic cycloadducts, while for the second, one class was synthesized by nucleophilic substitution of the bromide with the azide group. Comparative with conventional thermal heating (TH) under US irradiation, both types of reactions occur with substantially higher yields, shortened reaction time (from days to hours), lesser energy consumed, easier workup of the reaction, and smaller amounts of solvent required (at least three to five-fold less compared to TH), which make these reactions to be considered as energy efficient. The derivatized azatetracycle are blue emitters with λmax of fluorescence around 430-445 nm. A certain influence of the azatetracycle substituents concerning absorption and fluorescent properties was observed. Compounds anchored with a bulky azide group have shown decreased fluorescence intensity compared with corresponding bromides | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a azatetracyclic | |
| 650 | 4 | |a azides | |
| 650 | 4 | |a eco-friendly synthesis | |
| 650 | 4 | |a fluorescence | |
| 650 | 4 | |a heterogeneous catalytic bromination | |
| 650 | 4 | |a ultrasound irradiation | |
| 650 | 7 | |a Azides |2 NLM | |
| 650 | 7 | |a Pyrroles |2 NLM | |
| 700 | 1 | |a Ciobanu, Catalina-Ionica |e verfasserin |4 aut | |
| 700 | 1 | |a Mangalagiu, Ionel I |e verfasserin |4 aut | |
| 700 | 1 | |a Moldoveanu, Costel |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Molecules (Basel, Switzerland) |d 2004 |g 27(2022), 10 vom: 16. Mai |w (DE-627)NLM172073448 |x 1420-3049 |7 nnns |
| 773 | 1 | 8 | |g volume:27 |g year:2022 |g number:10 |g day:16 |g month:05 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.3390/molecules27103180 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 27 |j 2022 |e 10 |b 16 |c 05 | ||