Synthesis of a Series of Diaminoindoles

James S. Martin; Claire J. Mackenzie; Ian H. Gilbert

doi:10.1021/acs.joc.1c00652

Synthesis of a Series of Diaminoindoles

James S. Martin, Claire J. Mackenzie, Ian H. Gilbert (Lead / Corresponding author)

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2 Citations (Scopus)

97 Downloads (Pure)

Abstract

A selection of 3,4-diaminoindoles were required for a recent drug discovery project. To this end, a 10-step synthesis was developed from 4-nitroindole. This synthesis was subsequently adapted and used to synthesize 3,5-; 3,6-; and 3,7-diaminoindoles from the corresponding 5-, 6-, or 7-nitroindole. These novel intermediates feature orthogonal protecting groups that allow them to be further diversified. This is the first reported synthesis of these types of compounds.

Original language	English
Pages (from-to)	11333-11340
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	86
Issue number	17
Early online date	5 Aug 2021
DOIs	https://doi.org/10.1021/acs.joc.1c00652
Publication status	Published - 3 Sept 2021

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.1c00652Licence: CC BY

Final Published VersionFinal published version, 0.98 MBLicence: CC BY

Cite this

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title = "Synthesis of a Series of Diaminoindoles",

abstract = "A selection of 3,4-diaminoindoles were required for a recent drug discovery project. To this end, a 10-step synthesis was developed from 4-nitroindole. This synthesis was subsequently adapted and used to synthesize 3,5-; 3,6-; and 3,7-diaminoindoles from the corresponding 5-, 6-, or 7-nitroindole. These novel intermediates feature orthogonal protecting groups that allow them to be further diversified. This is the first reported synthesis of these types of compounds.",

author = "Martin, {James S.} and Mackenzie, {Claire J.} and Gilbert, {Ian H.}",

note = "We would like to acknowledge the University of Dundee for a Nicholl-Lindsey studentship (JM) and Medicines for Malaria Venture for financial support. This work was supported by a Wellcome Trust Centre Award [203134/Z/16/Z]. ",

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AU - Mackenzie, Claire J.

AU - Gilbert, Ian H.

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PY - 2021/9/3

Y1 - 2021/9/3

N2 - A selection of 3,4-diaminoindoles were required for a recent drug discovery project. To this end, a 10-step synthesis was developed from 4-nitroindole. This synthesis was subsequently adapted and used to synthesize 3,5-; 3,6-; and 3,7-diaminoindoles from the corresponding 5-, 6-, or 7-nitroindole. These novel intermediates feature orthogonal protecting groups that allow them to be further diversified. This is the first reported synthesis of these types of compounds.

AB - A selection of 3,4-diaminoindoles were required for a recent drug discovery project. To this end, a 10-step synthesis was developed from 4-nitroindole. This synthesis was subsequently adapted and used to synthesize 3,5-; 3,6-; and 3,7-diaminoindoles from the corresponding 5-, 6-, or 7-nitroindole. These novel intermediates feature orthogonal protecting groups that allow them to be further diversified. This is the first reported synthesis of these types of compounds.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

Synthesis of a Series of Diaminoindoles

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Synthesis of a Series of Diaminoindoles

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