Regio- and stereoselective one-pot synthesis of unknown oxazoline-fused pyridazines by 'Michael addition-pyridazine cyclization-oxazoline cyclization' cascade reactions of 4-chloro-1,2-diaza-1,3-butadienes with 3- dimethylaminopropenoates

Synlett

Volumn , Issue 19, 2007, Pages 2971-2974

  Attanasi, Orazio A ^a   Favi, Gianfranco ^a   Filippone, Paolino ^a   Golobič, Amalija ^b   Perrulli, Francesca R ^a   Stanovnik, Branko ^b   Svete, Jurij ^b  

^a UNIVERSITY OF URBINO   (Italy)

^b UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

1,2 diaza 1,3 butadienes; 3 dimethylaminopropenoates; Cyclizations; Michael additions; Oxazoline fused pyridazines

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 3 DIMETHYLAMINOPROPENOIC ACID DERIVATIVE; 4 CHLORO 1,2 DIAZA 1,3 BUTADIENE DERIVATIVE; ACRYLIC ACID DERIVATIVE; OXAZOLIDINE DERIVATIVE; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; MICHAEL ADDITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 37249079113     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990962     Document Type: Article

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58. 3 solution (5 mL) of 4-chloro-1,2-diaza-1,3- butadiene 1a-g (1 mmol) was added 3-dimethylaminopropenoate 2a-d (2 mmol) and DIPEA (1 mmol) and the reaction mixture was refluxed for the appropriate time (see Table 1). In order to obtain the intermediate II the reaction between 1a and 2a was heated to reflux for 5 h. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (eluent cyclohexane-EtOAc mixtures).
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