Effect of substituents on absorption and fluorescence properties of pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines

Abstract

A convenient route was successfully developed for the synthesis of novel heterocycles such as pyrazolo [3,4-b]pyrrolo [2,3-d]pyridines (PPP) from pyrazolo [3,4-b]pyridines in good yield. The PPP derivatives synthesized were further studied for their photophysical properties, and it was observed that absorption and emission λ max changed, owing to the substituent effect at 4 positions. These compounds were obtained from highly reactive starting materials, 5-aminopyrazoles and α-acetyl γ-butyrolactone.Résumé : On a mis au point une voie réactionnelle qui permet de réaliser la synthèse de nouveaux hétérocycles, telles les pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines (PPP) à partir de pyrazolo[3,4-b]pyridines, avec de bons rendements. On a soumis les dérivés PPP synthétisés à des études de leurs propriétés photophysiques et on a observé que les valeurs des λmax de leurs absorptions et de leurs émissions varient sous l'effet d'un changement dans la nature des substituants en position 4. On a obtenu ces composés à partir de produits de départ très réactifs, soit les 5-aminopyrazoles et l'α-acé-tyl-γ-butyrolactone.

Synthesis of Polysubstituted Pyrazolo[3,4‐b]pyridine‐3‐Carbohydrazide and Pyrazolo[3,4‐d]pyridazine Derivatives

“…Recently, we have reported the synthesis of highly fluorescent pyrazolo[3,4‐ b ]‐pyrrolo‐[2,3‐ d ]‐pyridines . These reports and our ongoing interest in this field prompted us to synthesize new fluorescent pyrazolo[3,4‐ b ]pyridines.…”

Novel synthesis of 2‐aminoquinoline‐3‐carbaldehyde, benzo[b][1,8]naphthyridines and study of their fluorescence behavior

“…Using these reports and our earlier communication, in relation to fluorescence properties of dipyrazolopyridines (DPP) 13, pyrazolopyrrolopyridine (PPP) 14 and pyridine‐3‐carbonitriles 15, herein, we report the synthesis of benzo[ b ][1,8] naphthyridines 8 starting from 2‐aminoquinoline‐3‐carbaldehyde 7 (heterocyclic orthoaminoaldehyde). The photophysical properties of 8 were studied and compared absorption and emission maxima with reference to donor and acceptor substituents on it.…”

Synthesis and Antimicrobial Activities of Iminothioether Linkers on Cyclopenta[a]phenanthrene Derivatives

“…Recent discovery of benzo [1,6]naphthyridine as selective highly potent mammalian inhibitor of rapamycin (mTOR) for the treatment of cancer cell [13,14]. In view of all these reports we have synthesized bioactive naphthyridine heterocyclic derivatives using α-acetyl γ-butyrolactone and heterocyclic amines, [15][16][17][18][19][20][21] to investigate new derivatives of benzo[h] [1,6]naphthyridines. In this present communication we report the synthesis of C 7iminotiaoether linkers to cyclopenta[a]phenanthren-7-ylsulfanyl)-N-phenyl acetamide.…”