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)

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

2 Citations (Scopus)

57 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

Access to Document

10.1021/acs.joc.1c00652Licence: CC BY

Final Published VersionFinal published version, 0.98 MBLicence: CC BY

Cite this

@article{b2d7dc1389b0426ba061c564235eb496,

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]. ",

year = "2021",

month = sep,

day = "3",

doi = "10.1021/acs.joc.1c00652",

language = "English",

volume = "86",

pages = "11333--11340",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Synthesis of a Series of Diaminoindoles

AU - Martin, James S.

AU - Mackenzie, Claire J.

AU - Gilbert, Ian H.

N1 - 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].

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.

UR - http://www.scopus.com/inward/record.url?scp=85113839055&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.1c00652

DO - 10.1021/acs.joc.1c00652

M3 - Article

C2 - 34351743

SN - 0022-3263

VL - 86

SP - 11333

EP - 11340

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Synthesis of a Series of Diaminoindoles

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Wellcome Centre for Anti-Infectives Research

Cite this

Synthesis of a Series of Diaminoindoles

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Projects

Wellcome Centre for Anti-Infectives Research

Cite this