Synthesis of functionalized 1-methylchromeno[3,4-b]pyrrol-4(3H)-ones via the Barton–Zard reaction starting from pseudonitrosites

Daniil A. Rusanov; Alexander V. Samet; Vyacheslav V. Rusak; Victor V. Semenov

doi:10.1007/s10593-021-03004-3

Synthesis of functionalized 1-methylchromeno[3,4-b]pyrrol-4(3H)-ones via the Barton–Zard reaction starting from pseudonitrosites

Daniil A. Rusanov, Alexander V. Samet^*, Vyacheslav V. Rusak, Victor V. Semenov

^*Corresponding author for this work

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

5 Citations (Scopus)

Abstract

A method for the preparation of chromeno[3,4-b]pyrrol-4(3H)-ones via the synthesis of the corresponding 3-arylpyrrole-2-carboxylates from pseudonitrosites by the Barton–Zard reaction was developed. As a result of selective O-demethylation upon exposure to BBr₃, the lactone ring closes with the formation of substituted chromeno[3,4-b]pyrrolones in moderate yields. © 2021, Springer Science+Business Media, LLC, part of Springer Nature.

Original language	English
Pages (from-to)	944-948
Number of pages	5
Journal	Chemistry of Heterocyclic Compounds
Volume	57
Issue number	9
Online published	30 Sept 2021
DOIs	https://doi.org/10.1007/s10593-021-03004-3
Publication status	Published - Sept 2021
Externally published	Yes

Funding

This work was carried out with the financial support of the Russian Science Foundation (project No. 18-13-00044-P).

Research Keywords

Barton–Zard reaction
chromeno[3,4-b]pyrrol-4(3H)-ones
lamellarins
O-demethylation
propenylbenzenes
pseudonitrosites

Access Output

10.1007/s10593-021-03004-3

Other Access Options

Check CityUHK Library

Permanent Link

Right click to copy link

Cite this

@article{1d7e8fba7d10486ca27034787a6b40dd,

title = "Synthesis of functionalized 1-methylchromeno[3,4-b]pyrrol-4(3H)-ones via the Barton–Zard reaction starting from pseudonitrosites",

abstract = "A method for the preparation of chromeno[3,4-b]pyrrol-4(3H)-ones via the synthesis of the corresponding 3-arylpyrrole-2-carboxylates from pseudonitrosites by the Barton–Zard reaction was developed. As a result of selective O-demethylation upon exposure to BBr3, the lactone ring closes with the formation of substituted chromeno[3,4-b]pyrrolones in moderate yields. {\textcopyright} 2021, Springer Science+Business Media, LLC, part of Springer Nature.",

keywords = "Barton–Zard reaction, chromeno[3,4-b]pyrrol-4(3H)-ones, lamellarins, O-demethylation, propenylbenzenes, pseudonitrosites",

author = "Rusanov, {Daniil A.} and Samet, {Alexander V.} and Rusak, {Vyacheslav V.} and Semenov, {Victor V.}",

year = "2021",

month = sep,

doi = "10.1007/s10593-021-03004-3",

language = "English",

volume = "57",

pages = "944--948",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer",

number = "9",

}

Synthesis of functionalized 1-methylchromeno[3,4-b]pyrrol-4(3H)-ones via the Barton–Zard reaction starting from pseudonitrosites. / Rusanov, Daniil A.; Samet, Alexander V.; Rusak, Vyacheslav V. et al.
In: Chemistry of Heterocyclic Compounds, Vol. 57, No. 9, 09.2021, p. 944-948.

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

TY - JOUR

T1 - Synthesis of functionalized 1-methylchromeno[3,4-b]pyrrol-4(3H)-ones via the Barton–Zard reaction starting from pseudonitrosites

AU - Rusanov, Daniil A.

AU - Samet, Alexander V.

AU - Rusak, Vyacheslav V.

AU - Semenov, Victor V.

PY - 2021/9

Y1 - 2021/9

N2 - A method for the preparation of chromeno[3,4-b]pyrrol-4(3H)-ones via the synthesis of the corresponding 3-arylpyrrole-2-carboxylates from pseudonitrosites by the Barton–Zard reaction was developed. As a result of selective O-demethylation upon exposure to BBr3, the lactone ring closes with the formation of substituted chromeno[3,4-b]pyrrolones in moderate yields. © 2021, Springer Science+Business Media, LLC, part of Springer Nature.

AB - A method for the preparation of chromeno[3,4-b]pyrrol-4(3H)-ones via the synthesis of the corresponding 3-arylpyrrole-2-carboxylates from pseudonitrosites by the Barton–Zard reaction was developed. As a result of selective O-demethylation upon exposure to BBr3, the lactone ring closes with the formation of substituted chromeno[3,4-b]pyrrolones in moderate yields. © 2021, Springer Science+Business Media, LLC, part of Springer Nature.

KW - Barton–Zard reaction

KW - chromeno[3,4-b]pyrrol-4(3H)-ones

KW - lamellarins

KW - O-demethylation

KW - propenylbenzenes

KW - pseudonitrosites

UR - http://www.scopus.com/inward/record.url?scp=85116357136&partnerID=8YFLogxK

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-85116357136&origin=recordpage

U2 - 10.1007/s10593-021-03004-3

DO - 10.1007/s10593-021-03004-3

M3 - RGC 21 - Publication in refereed journal

AN - SCOPUS:85116357136

SN - 0009-3122

VL - 57

SP - 944

EP - 948

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

IS - 9

ER -

Synthesis of functionalized 1-methylchromeno[3,4-b]pyrrol-4(3H)-ones via the Barton–Zard reaction starting from pseudonitrosites

Abstract

Funding

Research Keywords

Access Output

Other Access Options

Permanent Link

Other Files and Links

Fingerprint

Cite this