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- Title
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.
- Authors
Shaabani, Ahmad; Hajishaabanha, Fatemeh; Mofakham, Hamid; Mahyari, Mojtaba; Lali, Bagher
- Abstract
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 H2O 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).
- Subjects
ISOCYANIDES; CYANIDES; NAPHTHALENE; POLYCYCLIC aromatic hydrocarbons; BENZENE
- Publication
Helvetica Chimica Acta, 2012, Vol 95, Issue 2, p246
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201100270