1-Tosyl-6-vinyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole-2-amine

Fiach B. Meany; Sarah O’Rourke; Paul V. Murphy

doi:10.3390/M1262

1-Tosyl-6-vinyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole-2-amine

Fiach B. Meany
, Sarah O’Rourke
, Paul V. Murphy

Infectious Disease

University of Galway

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

Abstract

The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to furnish the title compound, which was characterized by 1H-NMR and ¹³C-NMR spectroscopy.

Original language	English
Article number	M1262
Journal	MolBank
Volume	2021
Issue number	3
DOIs	https://doi.org/10.3390/M1262
Publication status	Published - Sep 2021

Keywords

2-aminoimidazole
Condensation
NMR spectroscopy
Natural products
Synthesis

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10.3390/M1262

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title = "1-Tosyl-6-vinyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole-2-amine",

abstract = "The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to furnish the title compound, which was characterized by 1H-NMR and 13C-NMR spectroscopy.",

keywords = "2-aminoimidazole, Condensation, NMR spectroscopy, Natural products, Synthesis",

author = "Meany, \{Fiach B.\} and Sarah O{\textquoteright}Rourke and Murphy, \{Paul V.\}",

note = "Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2021",

month = sep,

doi = "10.3390/M1262",

language = "English",

volume = "2021",

journal = "MolBank",

issn = "1422-8599",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

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TY - JOUR

T1 - 1-Tosyl-6-vinyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole-2-amine

AU - Meany, Fiach B.

AU - O’Rourke, Sarah

AU - Murphy, Paul V.

PY - 2021/9

Y1 - 2021/9

N2 - The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to furnish the title compound, which was characterized by 1H-NMR and 13C-NMR spectroscopy.

AB - The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to furnish the title compound, which was characterized by 1H-NMR and 13C-NMR spectroscopy.

KW - 2-aminoimidazole

KW - Condensation

KW - NMR spectroscopy

KW - Natural products

KW - Synthesis

UR - https://www.scopus.com/pages/publications/85112271870

U2 - 10.3390/M1262

DO - 10.3390/M1262

M3 - Article

SN - 1422-8599

VL - 2021

JO - MolBank

JF - MolBank

IS - 3

M1 - M1262

ER -

1-Tosyl-6-vinyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole-2-amine

Abstract

Keywords

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