Pseudonitrosites as masked nitroalkenes in the Barton–Zard pyrrole synthesis

Daniil A. Rusanov; Andrey B. Myshlyavtsev; Eugenia A. Silyanova; Alexander V. Samet; Victor V. Semenov

doi:10.1016/j.mencom.2020.07.026

Pseudonitrosites as masked nitroalkenes in the Barton–Zard pyrrole synthesis

Daniil A. Rusanov, Andrey B. Myshlyavtsev, Eugenia A. Silyanova, Alexander V. Samet^*, Victor V. Semenov

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

3 Citations (Scopus)

Abstract

3-Aryl-4-methylpyrrole-2-carboxylates were prepared via the Barton–Zard reaction using pseudonitrosites as a source of the corresponding nitroalkenes. The starting pseudonitrosites were, in turn, obtained via addition of N₂O₃ to propenylbenzenes available from the natural plant essential oils. © 2020 Mendeleev Communications. Published by ELSEVIER B.V. on behalf of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences.

Original language	English
Pages (from-to)	485-486
Number of pages	2
Journal	Mendeleev Communications
Volume	30
Issue number	4
DOIs	https://doi.org/10.1016/j.mencom.2020.07.026
Publication status	Published - Jul 2020
Externally published	Yes

Funding

This research was financially supported by the Russian Science Foundation (project no. 18-13-00044). Authors are grateful to Dr. Dmitry V. Tsyganov for helpful discussion.

Research Keywords

Barton–Zard reaction
isomerization
lamellarins
propenylbenzenes
pseudonitrosites
pyrroles

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10.1016/j.mencom.2020.07.026

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title = "Pseudonitrosites as masked nitroalkenes in the Barton–Zard pyrrole synthesis",

abstract = "3-Aryl-4-methylpyrrole-2-carboxylates were prepared via the Barton–Zard reaction using pseudonitrosites as a source of the corresponding nitroalkenes. The starting pseudonitrosites were, in turn, obtained via addition of N2O3 to propenylbenzenes available from the natural plant essential oils. {\textcopyright} 2020 Mendeleev Communications. Published by ELSEVIER B.V. on behalf of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences.",

keywords = "Barton–Zard reaction, isomerization, lamellarins, propenylbenzenes, pseudonitrosites, pyrroles",

author = "Rusanov, {Daniil A.} and Myshlyavtsev, {Andrey B.} and Silyanova, {Eugenia A.} and Samet, {Alexander V.} and Semenov, {Victor V.}",

year = "2020",

month = jul,

doi = "10.1016/j.mencom.2020.07.026",

language = "English",

volume = "30",

pages = "485--486",

journal = "Mendeleev Communications",

issn = "0959-9436",

publisher = "Mendeleevskie Soobshcheniya",

number = "4",

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TY - JOUR

T1 - Pseudonitrosites as masked nitroalkenes in the Barton–Zard pyrrole synthesis

AU - Rusanov, Daniil A.

AU - Myshlyavtsev, Andrey B.

AU - Silyanova, Eugenia A.

AU - Samet, Alexander V.

AU - Semenov, Victor V.

PY - 2020/7

Y1 - 2020/7

N2 - 3-Aryl-4-methylpyrrole-2-carboxylates were prepared via the Barton–Zard reaction using pseudonitrosites as a source of the corresponding nitroalkenes. The starting pseudonitrosites were, in turn, obtained via addition of N2O3 to propenylbenzenes available from the natural plant essential oils. © 2020 Mendeleev Communications. Published by ELSEVIER B.V. on behalf of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences.

AB - 3-Aryl-4-methylpyrrole-2-carboxylates were prepared via the Barton–Zard reaction using pseudonitrosites as a source of the corresponding nitroalkenes. The starting pseudonitrosites were, in turn, obtained via addition of N2O3 to propenylbenzenes available from the natural plant essential oils. © 2020 Mendeleev Communications. Published by ELSEVIER B.V. on behalf of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences.

KW - Barton–Zard reaction

KW - isomerization

KW - lamellarins

KW - propenylbenzenes

KW - pseudonitrosites

KW - pyrroles

UR - http://www.scopus.com/inward/record.url?scp=85088986500&partnerID=8YFLogxK

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-85088986500&origin=recordpage

U2 - 10.1016/j.mencom.2020.07.026

DO - 10.1016/j.mencom.2020.07.026

M3 - RGC 21 - Publication in refereed journal

AN - SCOPUS:85088986500

SN - 0959-9436

VL - 30

SP - 485

EP - 486

JO - Mendeleev Communications

JF - Mendeleev Communications

IS - 4

ER -

Pseudonitrosites as masked nitroalkenes in the Barton–Zard pyrrole synthesis

Abstract

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Research Keywords

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