Solvent-Controlled Divergent Syntheses of Polycyclic N-Fused Heteroaromatics (Synthesis. 2020, 52(19):2841-56)

Authors: Anuradha Dagar, Dirgha Raj Joshi , Ikyon Kim∗

Abstract

Due to a growing interest in aza-fused polyaromatic systems among various sciences, enormous attention has been continuously paid to designing and synthesizing novel chemotypes of N-fused hetero­cycles. During the course of continued efforts in this line, it was found that divergent access to new polycyclic N-fused heteroaromatics was enabled by the choice of reaction solvent. Described herein are solvent-controlled selective approaches to three novel N-fused azacycles, benzo-[d]imidazole-pyrrolo[1,2-a]pyrazine hybrids, under mild conditions. The plausible reaction mechanism for each class of compound is suggested as well.

Research output as part of PhD work

  1. Synthesis of Poly-Functionalized Indolizines via [5+1] Annulative Access to Pyridines (Adv. syn. Cat., 2021, 363, 23, 5330-5335).
  2. Regioselective Synthesis of 1-Cyano-3-arylindolizines: Construction of Pyrrole via DDQ-Mediated Ring Closure of Cyclopropyl Pyridines
  3. Domino [4 + 2] Annulation Access to Quinone–Indolizine Hybrids: Anticancer N-Fused Polycycles (J. Org. Chem. 2020, 85, 16, 10994-1005).
  4. Michael-Aldol-Double Elimination Cascade to Make Pyridines: Use of Chromone for the Synthesis of Indolizines (J. Org. Chem. 2021, 86, 15, 10235–10248). (Adv. Synth. Cat., 2022, July 25).
  5. One-pot access to 2-amino-3-arylbenzofurans: direct entry to polyheterocyclic chemical space (Org. Biomol. Chem., 2020,18, 8119-8140).
  6.   Facile Access to 3, 4-Disubstituted 2H-Chromenes via Domino [4+ 2] Annulation (Synthesis 2021; 53(08): 1503-1512).
  7. Solvent-Controlled Divergent Syntheses of Polycyclic N-Fused Heteroaromatics (Synthesis. 2020, 52(19):2841-56).
  8. Benzofuro [2, 3-c] isoquinolines as novel AIEgens: Modulation of AIE characteristics by a single methoxy group. (Dyes and Pigments. 2022 Jul 21:110584).
  9.   Generation of a Poly-Functionalized Indolizine Scaffold and Its Anticancer Activity in Pancreatic Cancer Cells. (Bioorganic Chemistry. 2022; 126: 105877).
  10. BF3.OEt2-Catalyzed One-pot Three-component Access to Diarymethylazides (Tetrahedron Letters. 2021, 67, 152820).

Other research articles

  1. Detergent Use Practices in Nepal: A Cross-Sectional Online Survey. Current Journal of Applied Science and Technology. 2020 Dec 4:111-8. Doi: 10.9734/cjast/2020/v39i3631079.
  2. Effect of Health Insurance Program in Social Security in Kailali District, Nepal. 2020; 4 (2): 1-5. Acta Scientific Pharmaceutical Sciences.
  3. Study of In-vitro Antioxidant and Antibacterial activity of leaf extract of Azadirachta indica, and Ocimum sanctum in different organic solvents and Cow urine.  Journal of Drug Delivery and Therapeutics. 10.1-s (2020): 90-95. Doi: 10.22270/jddt.v10i1-s.3908.
  4. Anti-urolithiatic Property of Crataeva nurvala Root and Bark from Nepal on Ethylene Glycol induced Urolithiatic Mice. Journal of Pharmaceutical Sciences and Research. 2020 May 1;12(5):658-62.
  5. Personal Hygiene and Sanitary Practices among the School Girls in Dhangadhi, Nepal. advance.sagepub.com/articles/preprint. 2021.
  6. In-vitro Comparison of Anti-urolithiatic Effect of Crataeva nurvala, Zea mays (Corn Silk) and Ayurvedic Formulation Neeri Tablet. Int. J. Pharm. Sci. Rev. Res., 66(1), 2021; 07: 26-30.

Benzofuro [2, 3-c] isoquinolines as novel AIEgens: Modulation of AIE characteristics by a single methoxy group

Authors: Suzi Kim, Jae hyun Park, Dirgha RajJoshi, Na Keum Lee, Hang Le Bich Pham, Linh Khanh Chung, Min Joo Kang, Young gwan Kim, Ikyon Kim, Jeeyeon Lee

Abstract

Here, we report benzofuro[2,3-c]isoquinolines (FiQ) as novel blue AIEgens, in which a -OMe group substituent plays a crucial role in modulating intermolecular interactions, inducing a marked increase in emission of up to 150- and 460-fold in the aggregate and solid states, respectively. Our single-crystal X-ray diffraction analysis revealed that the edge-to-face interactions among phenyl groups generate tight networks that rigidify the assembled structures, resulting in AIE.