N‐Amino‐1,8‐Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono‐N‐Substituted Hydrazines and Hydrazides

Abstract

A new route to synthesis of various mono-Nsubstituted hydrazines and hydrazides by involving in a new CÀ 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 CÀ 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-1,8naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.

Halogen-Bonding Interaction-Mediated Efficient Iodine Capture of Highly Nitrogen-Functionalized Hyper-Crosslinked Polymers

“…The nucleophilic substitution reaction of P-OTs with an inordinate amount of hydrazine monohydrate produced a hydrazine-functionalized HCP ( P-Hz ). According to the previously reported results by Kumar and co-workers, the terminal nitrogen atom of the hydrazino group could further react with electrophiles to obtain the dialkylated hydrazine . The reaction of P-OTs with NaN 3 in DMF at 85 °C produced an azido-functionalized HCP ( P-Az ) that can be further reacted via the Staudinger reduction reaction with PPh 3 to afford an amine-modified HCP ( P-Am ).…”

“…According to the previously reported results by Kumar and co-workers, the terminal nitrogen atom of the hydrazino group could further react with electrophiles to obtain the dialkylated hydrazine. 37 The reaction of P-OTs with NaN 3 in DMF at 85 °C produced an azido-functionalized HCP (P-Az) that can be further reacted via the Staudinger reduction reaction with PPh 3 to afford an amine-modified HCP (P-Am). Moreover, the nitrogen-free HCP analogue was also prepared from benzene and toluene to afford P-Bz and P-Tol, respectively, as experimental controls (Scheme 1b).…”

Highly Thermally Resistant Bisamide Gelators as Pharmaceutical Crystallization Media

“…Compound G1, which was previously described by Shanmuga et al for different purposes [18], was synthesized for the purposes of this work, and G2 were prepared from acid chloride and anhydrous hydrazine [19]. Compound G3 was prepared from G1 through an alkylation reaction employing KOH and hexyl bromide (Scheme 1) [20].…”