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

Abstract

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.

Colorimetric 3D printable base-detectors exploiting halocromic core-substituted naphthalenediimides

“…After the polymeric characterization, some investigations were conducted to evaluate the material's behavior in contact with aqueous vapors and liquid organic phases, to verify the material's compatibility with possible final applications. 30–32…”

“…After the polymeric characterization, some investigations were conducted to evaluate the material's behavior in contact with aqueous vapors and liquid organic phases, to verify the material's compatibility with possible final applications. [30][31][32] In this context, the thickness of the sensing material is crucial since very thin specimens have a faster response due to rapid diffusion processes, but low mechanical properties. 20 For this reason, a trade-off value of 0.5 mm was set (see ESI file and Fig.…”

Copper-Catalyzed Three-Component Synthesis of β-Hydroxysulfides from Styrene Oxide, Aryl Iodide, and Carbon Disulfide

“…For example, Yang and co-workers developed a copper-catalyzed domino synthesis of C-3 sulfenylated imidazo[1,2- a ]pyridine derivatives using carbon disulfide as a building block . In 2022, Guo and co-workers reported CS 2 as a convenient sulfur source for the synthesis of 2-thio-1 H -benzo[ d ]-imidazoles and 2-thiobenzo[ d ]oxazoles . Inspired by these elegant pioneering studies, we proposed a copper-catalyzed domino synthetic approach for the synthesis of β-hydroxysulfides via ring-opening coupling from styrene oxide, carbon disulfide, and iodobenzene.…”

“…15 In 2022, Guo and co-workers reported CS 2 as a convenient sulfur source for the synthesis of 2-thio-1H-benzo[d]-imidazoles and 2-thiobenzo[d]oxazoles. 16 Inspired by these elegant pioneering studies, we proposed a copper-catalyzed domino synthetic approach for the synthesis of β-hydroxysulfides via ringopening coupling from styrene oxide, carbon disulfide, and iodobenzene. Meanwhile, we also found that the corresponding (benzo[d]thiazol)-β-hydroxysulfide products can be obtained when using o-iodoaniline instead of iodobenzene (Scheme 1d).…”