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Synthesis 2013; 45(2): 171-173
DOI: 10.1055/s-0032-1317935
short paper
© Georg Thieme Verlag Stuttgart · New York

A Reliable Synthesis of 3-Amino-5-Alkyl and 5-Amino-3-Alkyl Isoxazoles

Leland Johnson
Novartis Institutes for Biomedical Research, Global Discovery Chemistry, 100 Technology Square, Cambridge, MA 02139, USA   Fax: +1(617)8717044   Email: nello.mainolfi@novartis.com
,
James Powers
Novartis Institutes for Biomedical Research, Global Discovery Chemistry, 100 Technology Square, Cambridge, MA 02139, USA   Fax: +1(617)8717044   Email: nello.mainolfi@novartis.com
,
Fupeng Ma
Novartis Institutes for Biomedical Research, Global Discovery Chemistry, 100 Technology Square, Cambridge, MA 02139, USA   Fax: +1(617)8717044   Email: nello.mainolfi@novartis.com
,
Keith Jendza
Novartis Institutes for Biomedical Research, Global Discovery Chemistry, 100 Technology Square, Cambridge, MA 02139, USA   Fax: +1(617)8717044   Email: nello.mainolfi@novartis.com
,
Bing Wang
Novartis Institutes for Biomedical Research, Global Discovery Chemistry, 100 Technology Square, Cambridge, MA 02139, USA   Fax: +1(617)8717044   Email: nello.mainolfi@novartis.com
,
Erik Meredith
Novartis Institutes for Biomedical Research, Global Discovery Chemistry, 100 Technology Square, Cambridge, MA 02139, USA   Fax: +1(617)8717044   Email: nello.mainolfi@novartis.com
,
Nello Mainolfi*
Novartis Institutes for Biomedical Research, Global Discovery Chemistry, 100 Technology Square, Cambridge, MA 02139, USA   Fax: +1(617)8717044   Email: nello.mainolfi@novartis.com
› Author Affiliations
Further Information

Publication History

Received: 24 October 2012

Accepted after revision: 29 November 2012

Publication Date:
19 December 2012 (online)

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Abstract

A reliable procedure that can be used to access a wide range of 3-amino-5-alkyl and 5-amino-3-alkyl isoxazoles was developed. Reaction temperature and pH were key factors that determined the regioselectivity of the two reactions.

Key words

heterocycles - regioselectivity - condensation - medicinal chemistry - imines

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

  • References


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