Direct Minisci-Type C-H Amidation of Purine Bases

David T. Mooney; Peter R. Moore; Ai-Lan Lee

doi:10.1021/acs.orglett.2c03206

Direct Minisci-Type C-H Amidation of Purine Bases

David T. Mooney, Peter R. Moore, Ai-Lan Lee

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

15 Citations (Scopus)

69 Downloads (Pure)

Abstract

A method for the C–H carboxyamidation of purines has been developed that is capable of directly installing primary, secondary, and tertiary amides. Previous Minisci-type investigations on purines were limited to alkylations and arylations. Herein, we present the first method for the direct C–H amidation of a wide range of purines: xanthine, guanine, and adenine structures, including guanosine- and adenosine-type nucleosides. The Minisci-type reaction is also metal-free, cheap, operationally simple, scalable, and applicable to late-stage functionalizations of biologically important molecules.

Original language	English
Pages (from-to)	8008–8013
Number of pages	6
Journal	Organic letters
Volume	24
Issue number	43
Early online date	26 Oct 2022
DOIs	https://doi.org/10.1021/acs.orglett.2c03206
Publication status	Published - 4 Nov 2022

Access to Document

10.1021/acs.orglett.2c03206Licence: CC BY

Download pdf
© 2022 The Authors.
Final published version, 1.74 MBLicence: CC BY

Cite this

@article{76fbdf1e11ae4d80890fa41575a8572d,

title = "Direct Minisci-Type C-H Amidation of Purine Bases",

abstract = "A method for the C–H carboxyamidation of purines has been developed that is capable of directly installing primary, secondary, and tertiary amides. Previous Minisci-type investigations on purines were limited to alkylations and arylations. Herein, we present the first method for the direct C–H amidation of a wide range of purines: xanthine, guanine, and adenine structures, including guanosine- and adenosine-type nucleosides. The Minisci-type reaction is also metal-free, cheap, operationally simple, scalable, and applicable to late-stage functionalizations of biologically important molecules.",

author = "Mooney, {David T.} and Moore, {Peter R.} and Ai-Lan Lee",

note = "Funding Information: We would like to thank the Engineering and Physical Sciences Research Council and AstraZeneca for financial support (Industrial CASE Ph.D. studentship to D.T.M., Grant EP/V519522/1). Publisher Copyright: {\textcopyright} 2022 Authors. All rights reserved.",

year = "2022",

month = nov,

day = "4",

doi = "10.1021/acs.orglett.2c03206",

language = "English",

volume = "24",

pages = "8008–8013",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "43",

}

TY - JOUR

T1 - Direct Minisci-Type C-H Amidation of Purine Bases

AU - Mooney, David T.

AU - Moore, Peter R.

AU - Lee, Ai-Lan

N1 - Funding Information: We would like to thank the Engineering and Physical Sciences Research Council and AstraZeneca for financial support (Industrial CASE Ph.D. studentship to D.T.M., Grant EP/V519522/1). Publisher Copyright: © 2022 Authors. All rights reserved.

PY - 2022/11/4

Y1 - 2022/11/4

N2 - A method for the C–H carboxyamidation of purines has been developed that is capable of directly installing primary, secondary, and tertiary amides. Previous Minisci-type investigations on purines were limited to alkylations and arylations. Herein, we present the first method for the direct C–H amidation of a wide range of purines: xanthine, guanine, and adenine structures, including guanosine- and adenosine-type nucleosides. The Minisci-type reaction is also metal-free, cheap, operationally simple, scalable, and applicable to late-stage functionalizations of biologically important molecules.

AB - A method for the C–H carboxyamidation of purines has been developed that is capable of directly installing primary, secondary, and tertiary amides. Previous Minisci-type investigations on purines were limited to alkylations and arylations. Herein, we present the first method for the direct C–H amidation of a wide range of purines: xanthine, guanine, and adenine structures, including guanosine- and adenosine-type nucleosides. The Minisci-type reaction is also metal-free, cheap, operationally simple, scalable, and applicable to late-stage functionalizations of biologically important molecules.

UR - http://www.scopus.com/inward/record.url?scp=85140957066&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.2c03206

DO - 10.1021/acs.orglett.2c03206

M3 - Article

C2 - 36285836

SN - 1523-7060

VL - 24

SP - 8008

EP - 8013

JO - Organic letters

JF - Organic letters

IS - 43

ER -

Direct Minisci-Type C-H Amidation of Purine Bases

Abstract

Access to Document

Other files and links

Fingerprint