ChemInform Abstract: The Activity of Magnesium/Aluminum “Memory Effect” Reconstructed Hydrotalcites in the Microwave‐Assisted Synthesis of 2‐Benzimidazolethiol and Its Alkylated Derivatives.

Cruz-González, Deysi Y.; González-Olvera, Rodrigo; Ángeles-Beltrán, Deyanira; Negrón‐Silva, Guillermo E.; Santillán, Rosa

doi:10.1002/chin.201419131

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“…The traditional approach for the construction of 2-thio-1 H -benzo[ d ]imidazoles and 2-thiobenzo[ d ]oxazoles relies on the reaction of 1 H -benzo[ d ]imidazole-2-thiols/benzo[ d ]oxazole-2-thiols with (bromomethyl)benzenes through a nucleophilic substitution reaction process in the presence of bases at 60 °C (Scheme a) . Negrón-Silva and coworkers developed a microwave-assisted synthesis of 2-thio-1 H -benzo[ d ]imidazoles from 1,2-benzenediamines, CS 2 , and (bromomethyl)benzenes using reconstructed hydrotalcites (Scheme b) . In addition, Dong’s group reported a transition-metal-free cyclization of 1,2-phenylenediamines and 2-aminophenols with tetramethylthiuram disulfide to provide mercapto benzoheterocycles, and the subsequent C–S bond coupling with benzyl halides furnished the desired products in water (Scheme c) .…”

Section: Introductionmentioning

confidence: 99%

DBU-Promoted Deaminative Thiolation of 1H-Benzo[d]imidazol-2-amines and Benzo[d]oxazol-2-amines

et al. 2022

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A facile and efficient catalyst-/metal-/oxidant-free DBU-promoted deaminative thiolation reaction of 1H-benzo[d]imidazol-2-amines and benzo[d]oxazol-2-amines has been developed at room temperature conditions in a one-pot protocol. This practical three-component strategy represents a novel and environmentally friendly reaction pathway toward the straightforward synthesis of various 2-thio-1H-benzo[d]imidazoles and 2thiobenzo[d]oxazoles using carbon disulfide as a sulfur source through C−N bond cleavage and C−S bond formation process. Different types of 1H-benzo[d]imidazol-2-amines, benzo[d]oxazol-2-amines, and organic bromides are suitable substrates. The gram-scale and late-stage modification experiments provide the potential applications based on this methodology in the field of organic and medicinal chemistry.

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Section: Introductionmentioning

confidence: 99%