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Rearrangement Reactions of Divinyldiaziridines for the Enantioselective Synthesis of Diazepines and Benzodiazepines

Award Number: R15GM151707
ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES
OPDIV: NIH
AWARD CLASS: DISCRETIONARY
AWARD ACTIVITY TYPE: SCIENTIFIC/HEALTH RESEARCH (INCLUDES SURVEYS)

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Project Summary/Abstract Functionalized diaziridines are privileged scaffolds due to the multitude of reactivity profiles that can lead to the production of complex N,N-containing heterocyclic pharmacophores. Among these, diazepines and benzodiazepines stand out as one of the most pharmacologically relevant drug families. Thus, the chemical synthesis field has focused its attention on the development of novel methods for the synthesis of such highly complex heterocycles. This proposal aims to study the enantioselective rearrangement reactions of divinyldiaziridines under a series of reaction conditions for the systematic synthesis of optically pure diazepines and benzodiazepines. This proposal consists of 3 Aims. Aim 1: Enantioselective Synthesis of 1,2-, 1,3- and 1,4-Diazepines via the Stereoselective Rearrangement Reactions of Substituted Diaziridines. Aim 2: Enantioselective Rearrangement Reactions of Substituted Diaziridines for the Synthesis of Benzodiazepines. Aim 3: Diaza-Claisen Rearrangement for the Synthesis of Relevant Drug Scaffolds and Complex Heterocycles. The Moura-Letts laboratory has developed a strong research platform for the development of methods for the synthesis of heterocyclic scaffolds. This combination of skills and trained students would facilitate the successful implementation of the aims described in this proposal. The Claisen rearrangement reactions of divinyldiaziridines have never been reported. However, the knowledge acquired from diaziridine synthesis and their cycloadditions has served as a cornerstone for the design and rationalization of the proposed reactions. This work will allow efficient and systematic access to a large variety of unprecedented complex diazepines and benzodiazepines and thus help further elucidate their pharmacological profiles. The GML group is highly interested in developing organic methodologies for the synthesis and transformation of small heterocycles into more complex pharmacologically-relevant scaffolds. The success of this project would allow for the potential discovery of an unprecedented diaza-[3,3]-Claisen rearrangement and ring expansion pathways through the reaction of easily accessible vinyl and divinyldiaziridines. The impact of this project is also expanded by its ability to develop state-of-the-art organic chemistry skills in undergraduate students, high school students and returning veterans. These students have the potential to acquire a level of organic expertise that will qualify them to compete at the highest academic and industrial levels. 1


Issue Date FY	Funding FY	Legal Entity Name	Legal Entity Address	Legal Entity City	Legal Entity State	Legal Entity Zip Code	Legal Entity COUNTY	Legal Entity COUNTRY	Assistance Listing	Award Code	Budget Year	Action Date	Action Type	Action Amount

Issue Date FY: 2023 ( Subtotal = $449,777 )
2023	2023	ROWAN UNIVERSITY	201 MULLICA HILL RD RT 322	GLASSBORO	NJ	08028	GLOUCESTER	USA	Biomedical Research and Research Training	000	1	7/20/2023	NEW	$449,777
														Subtotal = $449,777

Grand Total All Awards = $449,777

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Rearrangement Reactions of Divinyldiaziridines for the Enantioselective Synthesis of Diazepines and Benzodiazepines

Award Number: R15GM151707

ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES

OPDIV: NIH

AWARD CLASS: DISCRETIONARY

AWARD ACTIVITY TYPE: SCIENTIFIC/HEALTH RESEARCH (INCLUDES SURVEYS)

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