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 |
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Authors: | Ahmad Shaabani Fatemeh Hajishaabanha Hamid Mofakham Mojtaba Mahyari Bagher Lali |
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Affiliation: | Department of Chemistry, Shahid Beheshti University, P.O. Box 19396‐4716, Tehran, Iran |
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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). |
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Keywords: | Multicomponent reactions Pyrazine‐2,3‐dicarbonitriles, 1,6‐dihydro‐6,6‐dimethyl‐ Benzo[g]quinoxalin‐2‐amine, 3,4‐dihydro‐ Quinoxalin‐2‐amines, 3,4‐dihydro‐3,3‐dimethyl‐ Isocyanide Pyrazine, dihydro‐ Benzoquinoxaline, dihydro‐ Quinoxaline, dihydro‐ |
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