349485-92-3

Upstream product

• 5690-46-0 2-amino-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 123-08-0 4-hydroxy-benzaldehyde 
• 94374-88-6 2-benzylideneamino-benzo[de]isoquinolin-1,3-dione 

Downstream Products

• 5690-46-0 2-amino-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 52211-82-2 4-hydroxylbenzaldehyde hydrazone 

Relevant academic research and scientific papers

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

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.

Synthesis of novel 2-amino-benzo[de]isoquinolin-1,3-dione derivatives

From a pioneer bioactive amino-benzoisoquinoline i.e. 2-amino-1H-benzo[de] isoquinolin-1,3-dione, a new series of Schiff's bases were prepared by the reaction of the active 2-amino group with a variety of aryl(hetero)aldehydes, isothiocyanides and acid anhydrides. The success of all reactions has been followed up by characterization of the synthesized target molecules through IR, Mass spectra and NMR analyses. The structural modifications were designed aiming at synthesis of valuable bioactive agents.