Files and links (1)
Published, Version of Record (VoR)CC BY V4.0, Open
Journal article
One-step synthesis of imidazoles from Asmic (anisylsulfanylmethyl isocyanide)
Beilstein journal of organic chemistry, v 17(1), pp 1499-1502
24 Jun 2021
PMID: 34239617
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Substituted imidazoles are readily prepared by condensing the versatile isocyanide Asmic, anisylsulfanylmethylisocyanide, with nitrogenous pi-electrophiles. Deprotonating Asmic with lithium hexamethyldisilazide effectively generates a potent nucleophile that efficiently intercepts nitrile and imine electrophiles to afford imidazoles. In situ cyclization to the imidazole is promoted by the conjugate acid, hexamethyldisilazane, which facilitates the requisite series of proton transfers. The rapid formation of imidazoles and the interchange of the anisylsulfanyl for hydrogen with Raney nickel make the method a valuable route to mono- and disubstituted imidazoles.
Metrics
Details
- Title
- One-step synthesis of imidazoles from Asmic (anisylsulfanylmethyl isocyanide)
- Creators
- Louis G. Mueller - Drexel UniversityAllen Chao - Abzena, 360 George Patterson Blvd, Bristol, PA 19007, USA.Embarek AlWedi - MSDFraser F. Fleming - Drexel University
- Publication Details
- Beilstein journal of organic chemistry, v 17(1), pp 1499-1502
- Publisher
- Beilstein-Institut
- Number of pages
- 4
- Grant note
- Drexel University
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000668148500001
- Scopus ID
- 2-s2.0-85108872354
- Other Identifier
- 991019168074204721
UN Sustainable Development Goals (SDGs)
This publication has contributed to the advancement of the following goals:
InCites Highlights
Data related to this publication, from InCites Benchmarking & Analytics tool:
- Collaboration types
- Industry collaboration
- Domestic collaboration
- Web of Science research areas
- Chemistry, Organic