Synthesis of Diamido N-Heterocyclic Imines (DAC = NH) Via Staudinger or Reductive N–N Bond Cleavage Approach
This report communicates the first examples of N-heterocyclic imines based on electrophilic diamido carbenes (DACs). While 2 is prepared by classical Staudinger synthesis, 4 is obtained via an unusual reductive N–N bond cleavage of an azine by HCl. The exocyclic C═N bond lengths in 2 and 4 are substantially shorter than those based on N-heterocyclic carbenes and cyclic (alkyl)(amino)carbene reflecting the electrophilic character of DACs.
Authors
- Kumar Vanka (ORCID: https://orcid.org/0000-0001-7301-7573)
- Sakya S. Sen (ORCID: https://orcid.org/0000-0002-4955-5408)
- Kajal Balayan (ORCID: https://orcid.org/0009-0003-1667-8190)
- Rajesh G. Gonnade (ORCID: https://orcid.org/0000-0002-2841-0197)
- Himanshu Sharma (ORCID: https://orcid.org/0000-0001-6333-4110)
Institutions
- National Chemical Laboratory (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- Organometallics
- Published
- 2025-05-27
- DOI
- https://doi.org/10.1021/acs.organomet.5c00120
- Citations
- 2
- Primary Topic
- Quinazolinone synthesis and applications
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Council of Scientific and Industrial Research, India
- University Grants Commission
- Science and Engineering Research Board