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Preparation of a New Friedländer Synthon, 2,3‐Diaminobenzene‐1,4‐dicarbaldehyde, and Its Application towards Synthesis of 1,10‐Phenanthrolines and Related Cyclophane
Author(s) -
Lu Yang,
Jahng Yurngdong
Publication year - 2019
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201800496
Subject(s) - synthon , chemistry , cyclophane , yield (engineering) , pyridine , organic chemistry , crystal structure , materials science , metallurgy
Summary of main observation and conclusion A new Friedländer synthon, 2,3‐diaminobenzene‐1,4‐dicarbaldehyde, was prepared from p‐xylene in 4 steps, of which the Friedländer reaction with acetaldehyde and acetone in a Schulenk bottle afforded 1,10‐phenathroline and neocuprine in 44% and 82% yield, respectively. The scope of the Friedländer reactions of 2,3‐diaminobenzene‐1,4‐dicarbaldehyde, including the synthesis of hexaazacyclic cyclophane with 1,10‐phenanthroline and pyridine units, was described