Volume 29, Issue 31
Heterocyclic Compounds
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ChemInform Abstract: Synthesis of Tetrazole Analogues of α-Amino Acids by Alkylation of a Schiff Base of α-Aminomethyltetrazole.

Y. SATOH

Y. SATOH

Metab. Cardiovasc. Dis. Res., Novartis Pharm. Corp., Summit, NJ 07901, USA

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S. DE LOMBAERT

S. DE LOMBAERT

Metab. Cardiovasc. Dis. Res., Novartis Pharm. Corp., Summit, NJ 07901, USA

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N. MARCOPULOS

N. MARCOPULOS

Metab. Cardiovasc. Dis. Res., Novartis Pharm. Corp., Summit, NJ 07901, USA

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J. MOLITERNI

J. MOLITERNI

Metab. Cardiovasc. Dis. Res., Novartis Pharm. Corp., Summit, NJ 07901, USA

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M. MOSKAL

M. MOSKAL

Metab. Cardiovasc. Dis. Res., Novartis Pharm. Corp., Summit, NJ 07901, USA

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J. TAN

J. TAN

Metab. Cardiovasc. Dis. Res., Novartis Pharm. Corp., Summit, NJ 07901, USA

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E. WALLACE

E. WALLACE

Metab. Cardiovasc. Dis. Res., Novartis Pharm. Corp., Summit, NJ 07901, USA

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First published: 20 June 2010

Abstract

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ChemInform Abstract

The Schiff base (IV) undergoes efficient alkylation with organic halides to yield products (VI) as analogues of α-amino acids. In order to demonstrate their usefulness, a dipeptide C-terminal tetrazole (VIII) is prepared. Interestingly, the boron-containing alkylation product can be subjected to Suzuki—Miyaura reaction to yield para-substituted phenylalanine tetrazole derivatives (X).

chemical structure image

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