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Isocyanide‐Based Three‐Component Synthesis of Highly Substituted 1,6‐Dihydro‐6,6‐dimethylpyrazine‐2,3‐dicarbonitrile, 3,4‐Dihydrobenzo[ g ]quinoxalin‐2‐amine, and 3,4‐Dihydro‐3,3‐dimethyl‐quinoxalin‐2‐amine Derivatives
Author(s) -
Shaabani Ahmad,
Hajishaabanha Fatemeh,
Mofakham Hamid,
Mahyari Mojtaba,
Lali Bagher
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100270
Subject(s) - chemistry , isocyanide , amine gas treating , catalysis , aryl , benzene , medicinal chemistry , alkyl , diamine , naphthalene , organic chemistry
A novel and efficient isocyanide‐based multicomponent reaction between alkyl or aryl isocyanides 1 , 2,3‐diaminomaleonitrile ( 2 ), naphthalene‐2,3‐diamines ( 6 ) or benzene‐1,2‐diamine ( 9 ), and 3‐oxopentanedioic acid ( 3 ) or Meldrum 's acid ( 4 ) or ketones 7 was developed for the ecologic synthesis, at room temperature under mild conditions, of 1,6‐dihydropyrazine‐2,3‐dicarbonitriles 5a – 5f in H 2 O without using any catalyst, and of 3,4‐dihydrobenzo[ g ]quinoxalin‐2‐amine and 3,4‐dihydro‐3,3‐dimethyl‐quinoxalin‐2‐amine derivatives 8a – 8g and 10a – 10e , respectively, in the presence of a catalytic amount of p ‐toluenesulfonic acid (TsOH) in EtOH, in good to excellent yields ( Scheme 1 ).