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Synlett 2011(14): 2009-2012  
DOI: 10.1055/s-0030-1260807
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Elaboration of Peptidomimetics Derived from a PADAM Approach: Synthesis of Polyfunctionalised 2(1H)-Pyrazinones via an Unexpected Aromatisation

Andrea Basso*, Luca Banfi, Giuseppe Guanti, Renata Riva, Paolo Tosatti
Dipartimento di Chimica e Chimica Industriale, Università di Genova, via Dodecaneso 31, 16146 Genova, Italy
Fax: +39(010)3536118; e-Mail: andrea.basso@unige.it;
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Publication History

Received 4 April 2011
Publication Date:
10 August 2011 (online)

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Abstract

When the PADAM (Passerini reaction-amine deprotection-acyl migration) strategy is applied to N-Boc amino acids, the resulting β-acylamino-α-hydroxyamides can be elaborated by secondary-alcohol oxidation, Boc deprotection, and intramolecular ­cyclisation. When TFA is employed to cleave the Boc group a spontaneous aromatisation to 2(1H)-pyrazinones is observed.

Key words

Passerini multicomponent reaction - isocyanides - heterocycles - ring closure - protecting groups - aromatisation

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1

Present address: P. Tosatti, School of Chemistry, University of Leeds, Leeds LS2 9JT, UK.

9

We have already applied this concept using the same PG for the α-amino aldehyde and the α-amino acid (ref. 6a).