1,5-electrocyclization of 1-alkyl-3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]- 1H-benzimidazol-3-ium bromides

L. M. Potikha; A. R. Turelyk; V. A. Kovtunenko

doi:10.1007/s10593-011-0780-6

1,5-electrocyclization of 1-alkyl-3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]- 1H-benzimidazol-3-ium bromides

L. M. Potikha^*, A. R. Turelyk, V. A. Kovtunenko

^*Corresponding author for this work

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

1 Citation (Scopus)

Abstract

Cyclization of 1-alkyl-3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]-1H- benzimidazol-3-ium bromides occurs in the presence of MeONa at a reduced temperature of 5-10°C via a 1,5-electrocyclization mechanism to give 3a,4-dihydro-3H-pyrrolo[1,2-a]benzimidazoles. These are unstable under the reaction conditions and are readily converted to {1-[2-(alkylamino)phenyl]-4- phenyl-1H-pyrrol-3-yl}(phenyl)methanones.

Original language	English
Pages (from-to)	452-455
Number of pages	4
Journal	Chemistry of Heterocyclic Compounds
Volume	47
Issue number	4
DOIs	https://doi.org/10.1007/s10593-011-0780-6
Publication status	Published - Jul 2011
Externally published	Yes

Keywords

1,5-electrocyclization
Benzimidazolium ylide
Pyrido[1,2-a]benzimidazole
Pyrrolo[1,2-a] benzimidazole

Access to Document

10.1007/s10593-011-0780-6

Cite this

@article{159214992a9b4b7590f014e587a87d44,

title = "1,5-electrocyclization of 1-alkyl-3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]- 1H-benzimidazol-3-ium bromides",

abstract = "Cyclization of 1-alkyl-3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]-1H- benzimidazol-3-ium bromides occurs in the presence of MeONa at a reduced temperature of 5-10°C via a 1,5-electrocyclization mechanism to give 3a,4-dihydro-3H-pyrrolo[1,2-a]benzimidazoles. These are unstable under the reaction conditions and are readily converted to {1-[2-(alkylamino)phenyl]-4- phenyl-1H-pyrrol-3-yl}(phenyl)methanones.",

keywords = "1,5-electrocyclization, Benzimidazolium ylide, Pyrido[1,2-a]benzimidazole, Pyrrolo[1,2-a] benzimidazole",

author = "Potikha, {L. M.} and Turelyk, {A. R.} and Kovtunenko, {V. A.}",

year = "2011",

month = jul,

doi = "10.1007/s10593-011-0780-6",

language = "English",

volume = "47",

pages = "452--455",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer",

number = "4",

}

TY - JOUR

T1 - 1,5-electrocyclization of 1-alkyl-3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]- 1H-benzimidazol-3-ium bromides

AU - Potikha, L. M.

AU - Turelyk, A. R.

AU - Kovtunenko, V. A.

PY - 2011/7

Y1 - 2011/7

N2 - Cyclization of 1-alkyl-3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]-1H- benzimidazol-3-ium bromides occurs in the presence of MeONa at a reduced temperature of 5-10°C via a 1,5-electrocyclization mechanism to give 3a,4-dihydro-3H-pyrrolo[1,2-a]benzimidazoles. These are unstable under the reaction conditions and are readily converted to {1-[2-(alkylamino)phenyl]-4- phenyl-1H-pyrrol-3-yl}(phenyl)methanones.

AB - Cyclization of 1-alkyl-3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]-1H- benzimidazol-3-ium bromides occurs in the presence of MeONa at a reduced temperature of 5-10°C via a 1,5-electrocyclization mechanism to give 3a,4-dihydro-3H-pyrrolo[1,2-a]benzimidazoles. These are unstable under the reaction conditions and are readily converted to {1-[2-(alkylamino)phenyl]-4- phenyl-1H-pyrrol-3-yl}(phenyl)methanones.

KW - 1,5-electrocyclization

KW - Benzimidazolium ylide

KW - Pyrido[1,2-a]benzimidazole

KW - Pyrrolo[1,2-a] benzimidazole

UR - http://www.scopus.com/inward/record.url?scp=80855130321&partnerID=8YFLogxK

U2 - 10.1007/s10593-011-0780-6

DO - 10.1007/s10593-011-0780-6

M3 - Article

AN - SCOPUS:80855130321

SN - 0009-3122

VL - 47

SP - 452

EP - 455

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

IS - 4

ER -

1,5-electrocyclization of 1-alkyl-3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]- 1H-benzimidazol-3-ium bromides

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this