Decomposition of Alkynyl Hydrazones: Synthesis of Allenoates, Dihaloallenoates, and Angularly Fused Tricyclic Azepines
Paru Jamwal, Akashdeep Sharma and Ramani Gurubrahamam*
*Department of Chemistry, Indian Institute of Technology Jammu, NH-44, PO Nagrota, Jagti, Jammu, Jammu and Kashmir 181221, India,
Email: guru.ramani
iitjammu.ac.in
P. Jamwal, A. Sharma, R. Gurubrahamam, Org. Lett., 2023, 25, 6607-6612.
DOI: 10.1021/acs.orglett.3c01994
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Abstract
Unprecedented decompositions of unprotected alkynyl hydrazones provide allenoates via DABCO-promoted Wolff-Kishner reduction, tetrasubstituted α,γ-dihaloallenoates in the presence of N-halosuccinimides, and functionalized tricyclic azepines in the presence of DBU.
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proposed mechanism
Key Words
allenes, iodination, bromination, NBS, NIS
ID: J54-Y2023
