N-amino- ​1,​8-​naphthalimide is a regenerated protecting group for selective synthesis of mono N-substituted hydrazines and hydrazides

Chemistry. 2021 Oct 19. doi: 10.1002/chem.202102593. Online ahead of print.ABSTRACTWe have invented a new route to synthesis of various mono N-substituted hydrazines and hydrazides by involving in a new C-N bond formation using N-amino-​1,​8-​naphthalimide as a regenerated precursor. 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 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 alkylidene hydrazine from aldehydes; synthesis of N-aminoazacycloalkanes from dihalo alkanes; developed a synthon for 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.PMID:34664751 | DOI:10.1002/chem.202102593

Source: Chemistry - October 19, 2021 Category: Chemistry Authors: Venkataramana Parikibanda Manoj Kumar Mesram Yadaiah Chityala Yadagiri Swamy Parikibanda Source Type: research