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- Title
N‐Amino‐1,8‐Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono‐N‐Substituted Hydrazines and Hydrazides.
- Authors
Manoj Kumar, Mesram; Venkataramana, Parikibanda; Yadagiri Swamy, Parikibanda; Chityala, Yadaiah
- Abstract
A new route to synthesis of various mono‐N‐substituted hydrazines and hydrazides by involving in a new C−N bond formation by using N‐amino‐1,8‐naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8‐naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C−N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N‐amino‐1,8‐naphthalimide is suitable synthon for transformation for selective formation of mono‐substituted hydrazine and hydrazide derivatives. Those are selective mono‐amidation of hydrazine with acid halides; mono‐N‐substituted hydrazones from aldehydes; synthesis of N‐aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N‐dibenzylhydrazines and N‐benzylhydrazines from benzyl halides; synthesis of N‐amino‐amino acids from α‐halo esters. Ecofriendly reagent N‐amino‐1,8‐naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.
- Subjects
HYDRAZIDES; HYDRAZINES; BENZYL halides; HYDRAZINE derivatives; ALDEHYDES; HYDRAZINE
- Publication
Chemistry - A European Journal, 2021, Vol 27, Issue 70, p17713
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202102593