A simple one-pot 2-step N-1-alkylation of indoles with α-iminoketones toward the expeditious 3-step synthesis of N-1-quinoxaline-indoles

Guillermo Martinez-Ariza; Muhammad Ayaz; Christopher Hulme

doi:10.1016/j.tetlet.2013.09.113

A simple one-pot 2-step N-1-alkylation of indoles with α-iminoketones toward the expeditious 3-step synthesis of N-1-quinoxaline-indoles

Guillermo Martinez-Ariza
, Muhammad Ayaz
, Christopher Hulme

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

7 Scopus citations

Abstract

A straightforward procedure for the preparation of N-quinoxaline-indoles is presented. A base-catalyzed one-pot addition of indoles to a preformed α-iminoketone proceeds on the N-1 indole and the subsequent adduct undergoes an acid-mediated deprotection of an internal amino nucleophile, intramolecular cyclization, and final oxidation generating N-1-quinoxaline- indoles in good yield.

Original language	English (US)
Pages (from-to)	6719-6721
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	49
DOIs	https://doi.org/10.1016/j.tetlet.2013.09.113
State	Published - Dec 4 2013

Keywords

Indole
Multicomponent reaction
Privileged scaffolds
Quinoxaline
α-Iminoketone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.09.113

Cite this

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title = "A simple one-pot 2-step N-1-alkylation of indoles with α-iminoketones toward the expeditious 3-step synthesis of N-1-quinoxaline-indoles",

abstract = "A straightforward procedure for the preparation of N-quinoxaline-indoles is presented. A base-catalyzed one-pot addition of indoles to a preformed α-iminoketone proceeds on the N-1 indole and the subsequent adduct undergoes an acid-mediated deprotection of an internal amino nucleophile, intramolecular cyclization, and final oxidation generating N-1-quinoxaline- indoles in good yield.",

keywords = "Indole, Multicomponent reaction, Privileged scaffolds, Quinoxaline, α-Iminoketone",

author = "Guillermo Martinez-Ariza and Muhammad Ayaz and Christopher Hulme",

note = "Funding Information: We would like to acknowledge the support from the National Institutes of Health (Grant P41GM086190 ) and CONACyT/UA (doctoral scholarship 215981 for G.M.A.). We also thank Dr. Sue Roberts for X-ray structure confirmation and Dr. David Bishop for proofreading, editing, and preparing the final version of the text and graphics. ",

year = "2013",

month = dec,

day = "4",

doi = "10.1016/j.tetlet.2013.09.113",

language = "English (US)",

volume = "54",

pages = "6719--6721",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "49",

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TY - JOUR

T1 - A simple one-pot 2-step N-1-alkylation of indoles with α-iminoketones toward the expeditious 3-step synthesis of N-1-quinoxaline-indoles

AU - Martinez-Ariza, Guillermo

AU - Ayaz, Muhammad

AU - Hulme, Christopher

N1 - Funding Information: We would like to acknowledge the support from the National Institutes of Health (Grant P41GM086190 ) and CONACyT/UA (doctoral scholarship 215981 for G.M.A.). We also thank Dr. Sue Roberts for X-ray structure confirmation and Dr. David Bishop for proofreading, editing, and preparing the final version of the text and graphics.

PY - 2013/12/4

Y1 - 2013/12/4

N2 - A straightforward procedure for the preparation of N-quinoxaline-indoles is presented. A base-catalyzed one-pot addition of indoles to a preformed α-iminoketone proceeds on the N-1 indole and the subsequent adduct undergoes an acid-mediated deprotection of an internal amino nucleophile, intramolecular cyclization, and final oxidation generating N-1-quinoxaline- indoles in good yield.

AB - A straightforward procedure for the preparation of N-quinoxaline-indoles is presented. A base-catalyzed one-pot addition of indoles to a preformed α-iminoketone proceeds on the N-1 indole and the subsequent adduct undergoes an acid-mediated deprotection of an internal amino nucleophile, intramolecular cyclization, and final oxidation generating N-1-quinoxaline- indoles in good yield.

KW - Indole

KW - Multicomponent reaction

KW - Privileged scaffolds

KW - Quinoxaline

KW - α-Iminoketone

UR - https://www.scopus.com/pages/publications/84886946646

UR - https://www.scopus.com/pages/publications/84886946646#tab=citedBy

U2 - 10.1016/j.tetlet.2013.09.113

DO - 10.1016/j.tetlet.2013.09.113

M3 - Article

AN - SCOPUS:84886946646

SN - 0040-4039

VL - 54

SP - 6719

EP - 6721

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -

A simple one-pot 2-step N-1-alkylation of indoles with α-iminoketones toward the expeditious 3-step synthesis of N-1-quinoxaline-indoles

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 985092: Experimental Crystal Structure Determination

Cite this

A simple one-pot 2-step N-1-alkylation of indoles with α-iminoketones toward the expeditious 3-step synthesis of N-1-quinoxaline-indoles

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 985092: Experimental Crystal Structure Determination

Cite this