1069111-98-3Relevant academic research and scientific papers
Environmentally Friendly Synthesis of Indoline Derivatives using Flow-Chemistry Techniques
?rkényi, Róbert,Beke, Gyula,Riethmüller, Eszter,Szakács, Zoltán,Kóti, János,Faigl, Ferenc,éles, János,Greiner, István
, p. 6525 - 6532 (2017)
Flow chemistry proved to be a valuable technique to improve the synthesis route to melanin-concentrating hormone receptor 1 (MCHr1) antagonists with the 1H,2H,3H,4H,5H-[1,4]diazepino[1,7-a]indole scaffold. A one-step route for the heterogeneous catalytic hydrogenation of ethyl 4-(2-nitrophenyl)-3-oxobutanoate for the synthesis of ethyl 2-(2,3-dihydro-1H-indol-2-yl)acetate was developed, and the use of common reducing chemicals was avoided. N-Alkylation of the indoline nitrogen atom was also optimized by using a purpose-built flow reactor and by design of experiment (DoE). Applying an optimal set of parameters allowed us to decrease the amount of carcinogenic 1,2-dibromoethane used by a factor of 10. Additionally, nearly complete conversion was achieved in a fraction of the original reaction time (30 min vs. 4 d); therefore, the productivity (space-time yield) of the flow-reactor system was proven to be ca. 200 times higher than that of the batch process.
Exploring of indole derivatives for ESIPT emission: A new ESIPT-based fluorescence skeleton and TD-DFT calculations
Ayd?n, Hatice Gülten,Ekmekci, Zeynep,Kaya, Serdal,Keskin, Selbi,Menges, Nurettin
, (2021/08/23)
Appropriate synthesis methods gave six different indole derivatives substituted at the C-2 or C-3 position. ESIPT emission capacities of these derivatives were investigated. It was concluded that the indole derivative containing the 1,2-dicarbonyl group at the C-2 position has ESIPT emission. Although adding water to the DMSO solution of the ESIPT-based molecule (9:1) resulted in ESIPT quenching, steady-state measurements in MeOH did not occur ESIPT quenching. TD-DFT calculation for uncovering the ESIPT mechanism emerged that the ESIPT mechanism occurred as a barrierless process. The X-ray analysis and DFT conformational analysis revealed that NH and CO groups involving proton transfer mechanisms are in the cis position. A mono-exponential decay was observed in DMSO and MeOH solutions, in which lifetimes were measured as 6.1 and 5.5 ns, respectively. pH studies revealed that acidic and basic solutions of molecule 7 did not influence ESIPT emission.
Diastereodivergence and appendage diversity in the multicomponent synthesis of aryl-pyrrolo-tetrahydrocarbazoles
Royer, Daniel,Wong, Yung-Sing,Plé, Sophie,Chiaroni, Angèle,Diker, Khalid,Lévy, Jean
, p. 9607 - 9618 (2008/12/22)
A one-pot approach using a subsequent Cu(II)/Cu(I) catalysis and a highly diastereodivergent three-component reaction allow an easy access to various aryl-pyrrolo-tetrahydrocarbazoles with the control of up to four variable fragments and two different diastereoselectivities.
