Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C–N, and C–O Bond Formation at Room Temperature
Hegde, Rajeev V.
Rode, Haridas B.
Mane, Manoj Vasisht
Patil, Siddappa A.
Dateer, Ramesh B.
KAUST DepartmentKAUST Catalysis Center (KCC)
Online Publication Date2021-10-13
Print Publication Date2021-11-05
Embargo End Date2022-10-13
Permanent link to this recordhttp://hdl.handle.net/10754/672908
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AbstractAn exclusive synthesis of benzo-oxazine, benzo-oxazepine, and benzo-oxazocine from aryl propanal and 2-(hydroxyamino)phenyl alcohol under metal-free conditions is described. O atom transfer and formation of new C═O, C-N, and C-O bonds occur at room temperature to form six-, seven-, and eight-membered heterocycles under one-pot reaction conditions without using an external oxidant and base. The photophysical properties are studied using ultraviolet-visible absorption and photoluminescence. The mechanistic elucidation is well supported by control experiment and literature precedents.
CitationGhosh, A., Hegde, R. V., Rode, H. B., Ambre, R., Mane, M. V., Patil, S. A., … Dateer, R. B. (2021). Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C–N, and C–O Bond Formation at Room Temperature. Organic Letters. doi:10.1021/acs.orglett.1c02895
SponsorsThe authors thank DST-SERB, Government of India, for financial support through Research Grants SB/S2/RJN-042/2017 and ECR/2017/002207. This Letter is CSIR-IICT Communication IICT/Pubs./2021/289. The authors are also thankful for a Jain University Start-up Research Grant. The authors thank Dr. Ahipa T. N., Jain University, for valuable input during the study of photophysical properties.
PublisherAmerican Chemical Society (ACS)
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