Stereoselective methodology for the synthesis of an antifungal allylamine: Terbinafine

Siva S. Panda

doi:10.2174/15701786113106660078

Stereoselective methodology for the synthesis of an antifungal allylamine: Terbinafine

Siva S. Panda

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

The stereoselective synthesis of an antifungal drug, Terbinafine, bearing (E)-tert-butylenyne structural element as the side chain is achieved by coupling N-methyl-1-napthalene methanamine with 1-bromo-6,6-dimethyl-2E-hepten-4- yne in good yield. The new methodology avoids the use of toxic starting materials like acrolein and phosphorous pentachloride that were used in earlier reports. The structure was confirmed by IR, NMR, MS, and elemental analysis.

Original language	English (US)
Pages (from-to)	141-144
Number of pages	4
Journal	Letters in Organic Chemistry
Volume	11
Issue number	2
DOIs	https://doi.org/10.2174/15701786113106660078
State	Published - Feb 2014
Externally published	Yes

Keywords

Alkylation
Antifungal drug
Selective reduction
Stereoselective synthesis
Terbinafine

ASJC Scopus subject areas

Organic Chemistry
Biochemistry

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10.2174/15701786113106660078

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abstract = "The stereoselective synthesis of an antifungal drug, Terbinafine, bearing (E)-tert-butylenyne structural element as the side chain is achieved by coupling N-methyl-1-napthalene methanamine with 1-bromo-6,6-dimethyl-2E-hepten-4- yne in good yield. The new methodology avoids the use of toxic starting materials like acrolein and phosphorous pentachloride that were used in earlier reports. The structure was confirmed by IR, NMR, MS, and elemental analysis.",

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AB - The stereoselective synthesis of an antifungal drug, Terbinafine, bearing (E)-tert-butylenyne structural element as the side chain is achieved by coupling N-methyl-1-napthalene methanamine with 1-bromo-6,6-dimethyl-2E-hepten-4- yne in good yield. The new methodology avoids the use of toxic starting materials like acrolein and phosphorous pentachloride that were used in earlier reports. The structure was confirmed by IR, NMR, MS, and elemental analysis.

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KW - Selective reduction

KW - Stereoselective synthesis

KW - Terbinafine

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JO - Letters in Organic Chemistry

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Stereoselective methodology for the synthesis of an antifungal allylamine: Terbinafine

Abstract

Keywords

ASJC Scopus subject areas

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