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One-pot synthesis of 1,3-diazaheterocycles via hydroxylamine hydrochloride activation of anthranilamide/phenylenediamines and DMF derivatives.
- Source :
-
Tetrahedron . Mar2024, Vol. 154, pN.PAG-N.PAG. 1p. - Publication Year :
- 2024
-
Abstract
- The development of sustainable methods is highly desirable in synthetic organic chemistry. In this regard, we report hydroxylamine hydrochloride mediated, one-pot synthesis of 1,3-diazaheterocycles using anthranilamide or o -phenylenediamine with amides via transamidation under solvent free condition at 120–140 °C for 8–14 h. This method proceeds smoothly under metal- and oxidant-free conditions exhibited broad substrate scope with reference to both diamines derivatives and amides, resulted in corresponding 4(3 H)-quinazolinone (3) and benzimidazoles (5 & 6) (∼47 examples) in good to excellent yield (56–96 %). As an efficient and environmentally friendly access to a broad range of 4(3 H)-quinazolinones and benzimidazoles and the synthetic utility of this method was demonstrated by gram-scale operation, achieved >90 % yield. [Display omitted] [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 154
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 175833760
- Full Text :
- https://doi.org/10.1016/j.tet.2024.133866