Annulative Synthesis of Thiazoles and Oxazoles from Alkenyl Sulfoxides and Nitriles via Additive Pummerer Reaction | Zendy

Hori Mitsuki | Zendy; Nogi Keisuke | Zendy; Nagaki Aiichiro | Zendy; Yorimitsu Hideki | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

Annulative Synthesis of Thiazoles and Oxazoles from Alkenyl Sulfoxides and Nitriles via Additive Pummerer Reaction

Author(s) -

Hori Mitsuki,

Nogi Keisuke,

Nagaki Aiichiro,

Yorimitsu Hideki

Publication year - 2019

Publication title -

asian journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.846

H-Index - 44

eISSN - 2193-5815

pISSN - 2193-5807

DOI - 10.1002/ajoc.201900169

Subject(s) - chemistry , ketene , pummerer rearrangement , annulation , sulfoxide , organic chemistry , medicinal chemistry , combinatorial chemistry , acetic anhydride , catalysis

Pummerer‐based annulation of alkenyl sulfoxides, mainly ketene dithioacetal monoxides (KDMs), with nitriles has been developed. By means of trifluoromethanesulfonic anhydride (Tf 2 O) as an activator, additive Pummerer reaction and subsequent C−S‐bond‐forming cyclization from the nitrilium intermediates furnished the corresponding thiazoles. Moreover, the nitrilium intermediates proved to be interrupted intermolecularly by H 2 O to afford oxazoles instead of thiazoles.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research