Alternate, easy and practical synthesis of allylamines from acetyl derivatives of Baylis-Hillman adducts using methanolic ammonia

Synthesis

Volumn , Issue 5, 2006, Pages 813-816

  Pathak, Richa ^a   Singh, Vijay ^a   Nag, Som N ^a   Kanojiya, Sanjeev ^a   Batra, Sanjay ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Allylamine; Baylis Hillman; Methanolic ammonia; Stereoselective

Indexed keywords

AMMONIA; SYNTHESIS (CHEMICAL);

ALLYLAMINE; BAYLIS-HILLMAN; METHANOLIC AMMONIA; STEREOSELECTIVE;

AMINES;

2 AMINOMETHYL 3 (2 BROMOPHENYL)ACRYLONITRILE; 2 AMINOMETHYL 3 (2 CHLOROPHENYL)ACRYLONITRILE; 2 AMINOMETHYL 3 (2 FLUOROPHENYL)ACRYLONITRILE; 2 AMINOMETHYL 3 (4 FLUOROPHENYL)ACRYLONITRILE; 2 AMINOMETHYL 3 (4 METHYLPHENYL)ACRYLONITRILE; 2 AMINOMETHYL 3 (4 PHENOXYMETHYLPHENYL)ACRYLONITRILE; 2 AMINOMETHYL 3 (NAPHTH 2 YL)ACRYLONITRILE; 2 AMINOMETHYL 3 PHENYLACRYLONITRILE; ACETIC ACID DERIVATIVE; ALLYLAMINE; AMINOMETHYL 3 (4 CHLOROPHENYL)ACRYLONITRILE; AMMONIA; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 33644897833     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926337     Document Type: Article

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25. During extensive exploratory studies on the Baylis-Hillman derivatives we have observed that reaction between acetyl derivatives of Baylis-Hillman adducts and primary amines (ca 1-1.5-fold) always lead to tertiary amines (Figure 1) as the major product. However, the formation of such an amine can be reduced by using excess amine (ca. 4-fold) and adding acetyl derivative slowly under cold conditions. (Diagram presented). Figure 1 Structure of tertiary amines formed in the reaction of primary amines with Baylis-Hillman adducts.
26. 4OAc (5-6 mM) were carried out to establish the exact molecular weight of products.