RhIII-Catalyzed Synthesis of Isoquinolones and 2-Pyridones by Annulation of N-Methoxyamides and Nitroalkenes

Tyler J. Potter; Yuantao Li; Michael D. Ward; Jonathan A. Ellman

doi:10.1002/ejoc.201800745

Rh^III-Catalyzed Synthesis of Isoquinolones and 2-Pyridones by Annulation of N-Methoxyamides and Nitroalkenes

Tyler J. Potter, Yuantao Li, Michael D. Ward, Jonathan A. Ellman

Chemistry

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

Abstract

The Rh^III-catalyzed synthesis of 4-substituted isoquinolones and 2-pyridones by the annulation of N-methoxyamides and nitroalkenes has been developed. Both aliphatic and aromatic nitroalkenes were effective inputs. Annulations also proceeded for aromatic, alkenyl, and heteroaromatic C–H bond starting materials. Moreover, benzoic acid provided a novel nitro-dihydroisocoumarin. The structure and relative stereochemistry of this compound, which is an oil at room temperature, was determined unambiguously by single-crystal X-ray diffraction of its inclusion complex with a hydrogen-bonded host framework.

Original language	English (US)
Pages (from-to)	4381-4388
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	32
DOIs	https://doi.org/10.1002/ejoc.201800745
State	Published - Aug 31 2018

Keywords

Annulation
C–H activation
Nitroalkenes
Nitrogen heterocycles
Synthetic methods

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/ejoc.201800745

Cite this

@article{111141f30d834225862ffdc5a4f14f28,

title = "RhIII-Catalyzed Synthesis of Isoquinolones and 2-Pyridones by Annulation of N-Methoxyamides and Nitroalkenes",

abstract = "The RhIII-catalyzed synthesis of 4-substituted isoquinolones and 2-pyridones by the annulation of N-methoxyamides and nitroalkenes has been developed. Both aliphatic and aromatic nitroalkenes were effective inputs. Annulations also proceeded for aromatic, alkenyl, and heteroaromatic C–H bond starting materials. Moreover, benzoic acid provided a novel nitro-dihydroisocoumarin. The structure and relative stereochemistry of this compound, which is an oil at room temperature, was determined unambiguously by single-crystal X-ray diffraction of its inclusion complex with a hydrogen-bonded host framework.",

keywords = "Annulation, C–H activation, Nitroalkenes, Nitrogen heterocycles, Synthetic methods",

author = "Potter, {Tyler J.} and Yuantao Li and Ward, {Michael D.} and Ellman, {Jonathan A.}",

note = "Funding Information: This work was supported primarily by the National Institutes of Health (NIH) (R35GM122473). M. D. W. and Y. L. acknowledge support from the National Science Foundation through Award No. DMR-1308677 and the National Science Foundation (NSF) MRSEC Program (DMR-1400273). The authors also acknowledge Chunhua (Tony) Hu of the NYU X-ray diffraction facility for helpful discussions. Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = aug,

day = "31",

doi = "10.1002/ejoc.201800745",

language = "English (US)",

volume = "2018",

pages = "4381--4388",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "32",

}

TY - JOUR

T1 - RhIII-Catalyzed Synthesis of Isoquinolones and 2-Pyridones by Annulation of N-Methoxyamides and Nitroalkenes

AU - Potter, Tyler J.

AU - Li, Yuantao

AU - Ward, Michael D.

AU - Ellman, Jonathan A.

N1 - Funding Information: This work was supported primarily by the National Institutes of Health (NIH) (R35GM122473). M. D. W. and Y. L. acknowledge support from the National Science Foundation through Award No. DMR-1308677 and the National Science Foundation (NSF) MRSEC Program (DMR-1400273). The authors also acknowledge Chunhua (Tony) Hu of the NYU X-ray diffraction facility for helpful discussions. Publisher Copyright: © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/8/31

Y1 - 2018/8/31

N2 - The RhIII-catalyzed synthesis of 4-substituted isoquinolones and 2-pyridones by the annulation of N-methoxyamides and nitroalkenes has been developed. Both aliphatic and aromatic nitroalkenes were effective inputs. Annulations also proceeded for aromatic, alkenyl, and heteroaromatic C–H bond starting materials. Moreover, benzoic acid provided a novel nitro-dihydroisocoumarin. The structure and relative stereochemistry of this compound, which is an oil at room temperature, was determined unambiguously by single-crystal X-ray diffraction of its inclusion complex with a hydrogen-bonded host framework.

AB - The RhIII-catalyzed synthesis of 4-substituted isoquinolones and 2-pyridones by the annulation of N-methoxyamides and nitroalkenes has been developed. Both aliphatic and aromatic nitroalkenes were effective inputs. Annulations also proceeded for aromatic, alkenyl, and heteroaromatic C–H bond starting materials. Moreover, benzoic acid provided a novel nitro-dihydroisocoumarin. The structure and relative stereochemistry of this compound, which is an oil at room temperature, was determined unambiguously by single-crystal X-ray diffraction of its inclusion complex with a hydrogen-bonded host framework.

KW - Annulation

KW - C–H activation

KW - Nitroalkenes

KW - Nitrogen heterocycles

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=85050453162&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85050453162&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201800745

DO - 10.1002/ejoc.201800745

M3 - Article

AN - SCOPUS:85050453162

SN - 1434-193X

VL - 2018

SP - 4381

EP - 4388

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 32

ER -