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Synthesis of Highly Functionalized Tricyclic Chromenopyrazole Frameworks via Intramolecular Azomethine Imine 1,3‐Dipolar Cycloaddition (IAIDC)
Author(s) -
Bakthadoss Manickam,
Agarwal Vishal
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801269
Subject(s) - intramolecular force , cycloaddition , chemistry , imine , tricyclic , 1,3 dipolar cycloaddition , adduct , stereospecificity , aryl , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , alkyl
A general protocol for the synthesis of angularly substituted tricyclic chromenopyrazoles via an intramolecular azomethine imine 1,3‐dipolar cycloaddition (IAIDC) reaction of O ‐allylated salicylaldehydes (derived from bromo derivatives of Baylis‐Hillman adducts) and aryl hydrazines has been described for the first time. This reaction creates two rings (six and five‐membered) via the formation of one C–C bond and two C−N bonds. Moreover, the products are formed with two chiral centers with high diastereoselectivity and stereospecificity. Some of the synthesized compounds were examined for the fluorescent properties and found to exhibit strong fluorescence in the blue region.