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Dichloro‐Substituted 1,2‐Diazabuta‐1,3‐dienes as Highly Reactive Electrophiles in the Reaction with Amines and Diamines: Efficient Synthesis of α‐Hydrazo Amidinium Salts
Author(s) -
Shastin Alexey V.,
Sergeev Pavel G.,
Lukianova Anna I.,
Muzalevskiy Vasiliy M.,
Khrustalev Victor N.,
Dorovatovskii Pavel V.,
Nenajdenko Valentine G.
Publication year - 2018
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.201800441
Subject(s) - chemistry , electrophile , combinatorial chemistry , hydrazone , reaction conditions , amine gas treating , reactive intermediate , molecule , organic chemistry , catalysis
The reaction of 4,4‐dichloro‐1,2‐diazabuta‐1,3‐dienes with various amines and diamines was studied. We found that in this reaction, the starting diazabutadienes behave as highly reactive electrophiles to open up a straightforward route to the corresponding amidinium salts with a hydrazone functionality in the adjacent position. The reaction was found to be very general; as a rule, all the products could be prepared in almost quantitative yields. We also demonstrated that the prepared amidinium salts could be used as versatile building blocks for the synthesis of polyfunctional molecules.