Urea-Promoted Neat Synthesis of Fused Dihydroisoquinolines and Disubstituted Pyridines: A Mechanistic Observation with Molecular-Sensing Studies.

Autor: Azad SA; Department of Chemistry, Bidhannagar College, Salt Lake, Sector - I, Kolkata, 700064, India.; Department of Chemistry, University of Calcutta, Acharya Prafulla Chandra Road, Kolkata, 700009, India., Bera A; Department of Chemistry, Bidhannagar College, Salt Lake, Sector - I, Kolkata, 700064, India., Samanta J; Department of Chemistry, College of Engineering and Technology, SRM Institute of Science and Technology, Kattankulathur, Tamil Nadu, 603203, India., Sepay N; Department of Chemistry, Lady Brabourne College, Kolkata, 700 017, India., Jana R; Department of Chemistry, Shahid Matangini Hazra Govt. General Degree College for Women, West Bengal, India., Pal CK; Department of Chemistry, Bidhannagar College, Salt Lake, Sector - I, Kolkata, 700064, India., Molla MR; Department of Chemistry, University of Calcutta, Acharya Prafulla Chandra Road, Kolkata, 700009, India., Maiti D; Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai, Maharashtra, 400076, India., Samanta S; Department of Chemistry, Bidhannagar College, Salt Lake, Sector - I, Kolkata, 700064, India.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Mar 01; Vol. 30 (13), pp. e202303287. Date of Electronic Publication: 2024 Jan 12.
DOI: 10.1002/chem.202303287
Abstrakt: An efficient and short synthesis of fused dihydroisoquinolines, diaryl substituted pyridine derivatives in good to high yields has been established by using an environmentally safe, solvent-metal-oxidant-free tandem approach. In this article, we discuss how the electrocyclic reaction is more pronounced in the solid phase in the presence of urea, whereas the typical aza-Michael addition is more prominent in presence of arylamine in the solution phase for 3-(2-formylcycloalkenyl)acrylic ester derivative substrates. The wide range of substrates and urea-promoted neat synthesis made our approach more significant in medical and also analytical science. Moreover, an isoquinoline alkaloid decumbenine B analogue has been synthesized by using our newly developed neat methodology. We have also investigated the photophysical properties of the synthesized fused dihydroisoquinoline derivatives. One of the synthesized molecules was used as a sensor for the selective detection of toxic picric acid. Therefore, the effective neat synthesis and molecular sensing applications of these compounds made our approach more exciting in the field of heterocyclic chemistry.
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Databáze: MEDLINE
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