Thiazoles polycycliques. I. Substitution par les nucléophiles anioniques des dérivés 2‐méthylsulfonylés de la thiazolo[5,4<i>‐b</i>]‐pyridine et du benzothiazole

Bourdais, J.; Abenhaïm, D.; Sabourault, B.; Lorre, A.

doi:10.1002/jhet.5570130314

Cited by 18 publications

(1 citation statement)

References 27 publications

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“…Next, based on these results, we focused on 2-alkoxybenzothiazoles and 2-alkoxybenzoxazoles as the coupling partners, as shown in Scheme . First, the reaction of 1a with 2-methoxybenzothiazole in the presence of 3 mol % Rh 2 (Oct) 4 was performed in DCE at 100 °C for 80 min to provide an excellent yield of 4a (90%). The Z- stereochemical structure of 4a was confirmed by the 2D nuclear Overhauser effect spectroscopy (NOESY) analysis.…”

Section: Resultsmentioning

confidence: 99%

Rhodium(II)-Catalyzed Highly Selective 1,3-Insertion Reactions Using N-Sulfonyl-1,2,3-Triazoles with Heteroaryl Ethers or Heteroaryl Alcohols

et al. 2022

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The transformation of N-sulfonyl-1,2,3-triazoles via insertion/rearrangement is achieved using 2-hydroxybenzimidazole or 2-alkoxybenzothiazole over 3 mol % Rh 2 (Oct) 4 for the synthesis of α- ((1H-benzo[d]imidazol-2-yl)amino) ketones or (Z)-2-alkoxy-2-phenylethenamines. This regio-and stereoselective reaction proceeds under mild conditions, is tolerant of functional groups, and has a broad substrate scope. Notably, while the general rhodium-catalyzed reaction involves sigmatropic rearrangement from an allyl vinyl ether, the present synthetic methodology prevents rearrangement owing to the benzimidazole group, allowing access to (Z)-olefins.

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Section: Resultsmentioning

confidence: 99%