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Title: Selective Conversion of O-Succinimidyl Carbamates to N-(O-Carbamoyl)-Succinmonoamides and Ureas

Author
item VASILEVICH, NATALYA - TULANE HEALTH SCI. CTR.,
item Sachinvala, Navzer
item MASKOS, KAROL - TULANE UNIV., N. O., LA
item COY, DAVID - TULANE HEALTH SCI. CTR.

Submitted to: Tetrahedron Letters
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/28/2002
Publication Date: 4/1/2002
Citation: Vasilevich, N.I., Sachinvala, N.D., Maskos, K., Coy, D.H. 2002. Selective Conversion of O-Succinimidyl Carbamates to N-(O-Carbamoyl)-Succinmonoamides and Ureas. Tetrahedron Letters. 43:3443-3445.

Interpretive Summary: There is a great need for new compounds (or analogs) that belong to the class of materials called hydroxylamine derivatives because they are biologically very important, and new clinical and industrial uses for these derivatives need to be explored. Hydroxylamine analogs block nucleic acid (DNA) synthesis. They are mutagenic, detoxify harmful metals by binding to them, and display excellent antimalarial activity. In this paper, we showed the synthesis of new hydroxylamine derivatives called N-(O-carbamoyl)-succinmonoamides via a novel and generally useful reaction. Furthermore, we thoroughly explained the structures of all new compounds via a variety of modern analytical methods. This work will be useful to scientists and researchers in universities, clinics, and industries that are involvled in designing new drugs, pesticides, and metal detoxifying agents for clinical, exploratory, and other uses.

Technical Abstract: N-monoalkyl-O-succinimidyl carbamates reached with primary and secondary amines to produce ureas. However, N,N-dialkyl-O-succinimidyl-carbamates reacted with primary and secondary amines, via succinimide ring opening, to afford N-(O-carbamoyl)-succinmonoamide derivatives. This ring opening trend was also true with hydroxy and alkoxy nucleophiles. Herein, general methods for the synthesis and NMR characterization of N-)O-carbamoyl)-succinmonoamides are reported.