Department of Chemistry, University College of Science, Osmania University, Hyderabad, 500 007, India.
Chemistry Services, Excelra, NSL Arena Town centre, NSL SEZ, I.D.A. Uppal, Hyderabad, 500 039, India.
Chemistry. 2021 Dec 15;27(70):17713-17721. doi: 10.1002/chem.202102593. Epub 2021 Nov 5.
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.
发明了一种通过涉及新的 C-N 键形成，将 N-氨基-1,8-萘酰亚胺用作再生前体，来合成各种单-N-取代的肼和酰肼的新途径。苯胺和苯肼分别与 1,8-萘酐反应，然后进行肼解，就可以得到这些化合物的再生。该 C-N 二卤代烷的实用性和简单性；通过各种肼和酰肼的键形成协议，开发了一个合成子。N-氨基-1,8-萘酰亚胺是用于选择性形成单取代肼和酰肼衍生物的转化的合适的合成子。这些方法包括：与酸卤化物的肼的选择性单酰胺化；醛的单-N-取代腙；从乙醯基乙内醯胺骨架插入到羟衍生物的 N-氨基氮杂环烷；从卤代苄制备 N,N-二苄基肼和 N-苄基肼；从α-卤代酯合成 N-氨基氨基酸。在所有步骤中，通过肼解可以以良好的产率再生环保试剂 N-氨基-1,8-萘酰亚胺。
