Different behavior of the reaction between 1,2-diaza-1,3-butadienes and 1,2-diamines under solvent or solvent-free conditions

Synlett

Volumn , Issue 9, 2005, Pages 1474-1476

  Attanasi, Orazio A ^a   De Crescentini, Lucia ^a   Favi, Gianfranco ^a   Filippone, Paolino ^a   Lillini, Samuele ^a   Mantellini, Fabio ^a   Santeusanio, Stefania ^a  

^a UNIVERSITY OF URBINO   (Italy)

Author keywords

1,2 diaza 1,3 butadienes; Heterocyclic compounds; Michael additions; Pyrazine derivatives; Regioselectivity

Indexed keywords

1,2 DIAZA 1,3 BUTADIENE; 1,3 BUTADIENE; BROMINE DERIVATIVE; CARBON; DIAMINE; HETEROCYCLIC COMPOUND; PALLADIUM; PHENYLTRIMETHYLAMMONIUM; PHENYLTRIMETHYLAMMONIUM TRIBROMIDE; PIPERAZINE DERIVATIVE; PYRAZINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CYCLIZATION; MICHAEL ADDITION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 20544450097     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-868517     Document Type: Article

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24. 3: C, 58.42; H, 7.84; N, 18.17. Found: C, 58.50; H, 7.79; N, 18.23.
25. 2: C, 74.98; H, 5.30; N, 9.20. Found: C, 74.89; H, 5.25; N, 9.14.
26. General Procedure for Synthesis of Ethyl 3-Methylpyrazine-2-carboxylate (7d). A solution of 1,2-diaza-1,3-butadienes 1c,d (1 mmol) in EtOH (10 mL) was added dropwise to a magnetically stirred solution of 1,2-ethanediamine 2a (1.0 mmol) in EtOH (50 mL). The reaction was allowed to stand at r.t. until complete disappearance of 1,2-diaza-1,3-butadiene (monitored by silica gel TLC, 1 h). The reaction was then treated with Pd/C (110 mg, 5%) with magnetic stirring and was refluxed for 14 h. The mixture was filtered and the solvent evaporated under reduced pressure. Product 7d was purified by chromatography on silica gel (elution mixture: cyclohexane-EtOAc, 70:30).