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Synthesis 2006(5): 813-816  
DOI: 10.1055/s-2006-926337
PAPER
© Georg Thieme Verlag Stuttgart · New York

Alternate, Easy and Practical Synthesis of Allylamines from Acetyl Derivatives of Baylis-Hillman Adducts Using Methanolic Ammonia [1]

Richa Pathaka, Vijay Singha, Som N. Naga, Sanjeev Kanojiyab, Sanjay Batra*a
a Medicinal Chemistry Division, Central Drug Research Institute, Lucknow 226001, India
Fax: +91(522)2623405; Fax: +91(522)2623938; e-Mail: batra_san@yahoo.co.uk;
b SAIF Division, Central Drug Research Institute, Lucknow 226001, India
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Publication History

Received 16 August 2005
Publication Date:
07 February 2006 (online)

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Abstract

A methanolic ammonia-mediated alternate, easy and practical stereoselective synthesis of allylamines from the acetyl derivatives of Baylis-Hillman adducts is described.

Key words

Baylis-Hillman - allylamine - methanolic ammonia - stereoselective

1

CDRI Communication No. 6786.

1

CDRI Communication No. 6786.

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Singh V., Pathak R., Kanojiya S., Batra S.; Synlett; 2005, 2465.

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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.

Figure 1 Structure of tertiary amines formed in the reaction of primary amines with Baylis-Hillman adducts.

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Several experiments using ESI mass spectrometry technique in the presence of NH4OH and/or NH4OAc (5-6 mM) were carried out to establish the exact molecular weight of products.