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Effective Synthesis of ortho ‐Substituted Trithiophenol Amines by Miyazaki–Newman–Kwart Rearrangement
Author(s) -
Gjoka Blerina,
Romano Francesco,
Zonta Cristiano,
Licini Giulia
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100977
Subject(s) - chemistry , thiocarbamate , reductive amination , yield (engineering) , amination , thiocarbamates , combinatorial chemistry , amine gas treating , reductive elimination , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
An efficient synthesis of ortho ‐substituted trithiophenol amines from commercially available salicaldehydes by Miyazaki–Newman–Kwart rearrangement/threefold reductive amination is reported. The rearrangement has been carried out on salicaldehyde‐ O ‐thiocarbamates using microwave induced heating, which furnishes a series of thiosalicaldehyde‐ S ‐carbamates in high yield. The thiocarbamate has three roles: it enables effective S – O rearrangement, acts as a protecting group during the threefold reductive amination and can be easily removed under reductive conditions. The three‐step synthesis has an overall yield ranging from 30–35 %, and it enables access to a series of increasingly important C 3 v symmetric ligands in a structurally systematic way.