Document Type

Article

Publication Date

3-19-2020

Publication Title

Tetrahedron Letters

Volume

61

Issue

12

Pages

151632

Publisher Name

Elsevier

Abstract

The hydrochloride salt of ɑ-aminocyclobutanone protected as its dimethyl acetal 2,2-dimethoxycyclobutan-1-aminium chloride (3) has been prepared as a modular synthon for convenient access to cyclobutanone-containing lead inhibitors of hydrolase enzymes including serine proteases and metalloproteases. Protected ɑ-aminocyclobutanone 3 was converted to representative amide and sulfonamide-functionalized 2-aminocyclobutanone derivatives. Reaction of the amino acetal 3 with phenyl isothiocyanate afforded the bicyclic urea 1-hydroxyl-2,4-diazabicyclo[3.2.0]heptane-3-thione (9) as confirmed by a single crystal X-ray structure.

Comments

Author Posting © Elsevier Ltd, 2020. This is the author's version of the work. It is posted here by permission of Elsevier Ltd for personal use, not for redistribution. The definitive version was published in Tetrahedron Letters, Volume 61, Issue 12, March 2020. https://doi.org/10.1016/j.tetlet.2020.151632

Creative Commons License

Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

Available for download on Saturday, March 19, 2022

Share

COinS