A new synthetic approach to cyclic ureas through carbonylation using di- tert -butyl dicarbonate (boc anhydride) via one pot strategy.

Autor: Thrinadh Kumar R; Department of Chemistry, School of Applied Science and Humanities, Vignan's Foundation for Science Technology and Research, Vadlamudi, Guntur, Andhra Pradesh 522213, India. ravikottalanka@gmail.com.; Aragen Life Sciences Ltd, 28A, IDA Nacharam, Hyderabad, Telangana-500076, India., Makam P; Department of Chemistry, School of Applied and Life Sciences, Uttaranchal University, Arcadia Grant, P.O. Chandanwari, Premnagar, Dehradun, Uttarakhand-248007, India., Katari NK; Department of Chemistry, GITAM School of Science, GITAM Deemed to be University, Hyderabad, Telangana-502329, India. nkatari@gitam.edu., Kottalanka RK; Department of Chemistry, School of Applied Science and Humanities, Vignan's Foundation for Science Technology and Research, Vadlamudi, Guntur, Andhra Pradesh 522213, India. ravikottalanka@gmail.com.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2023 Oct 04; Vol. 21 (38), pp. 7821-7830. Date of Electronic Publication: 2023 Oct 04.
DOI: 10.1039/d3ob01330h
Abstrakt: A new approach has been successfully employed to synthesize cyclic ureas via carbonylation, utilizing Boc anhydride and employing K 2 CO 3 as a base along with N , N -dimethylformamide as the solvent. Remarkably high yields were achieved using K 2 CO 3 in conjunction with (Boc) 2 O, enabling the streamlined preparation of benzimidazolones and 2-benzoxazolones within a single reaction vessel. Significantly, this approach obviates the necessity for using any dangerous reagents, rendering it environmentally friendly, and its key benefit lies in being a metal-free system. The method stands out for its efficiency, concise pathway, optimization from readily accessible starting materials, and ease of execution. The resulting benzimidazolones and 2-benzoxazolones were thoroughly characterized using techniques including LCMS, 1 H NMR, and 13 C NMR.
Databáze: MEDLINE