# Rearrangement Reactions of Divinyldiaziridines for the Enantioselective Synthesis of Diazepines and Benzodiazepines - Supplemental for Equipment Purchase

> **NIH NIH R15** · ROWAN UNIVERSITY · 2024 · $98,800

## Abstract

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.
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## Key facts

- **NIH application ID:** 11009708
- **Project number:** 3R15GM151707-01S1
- **Recipient organization:** ROWAN UNIVERSITY
- **Principal Investigator:** Gustavo Moura-Letts
- **Activity code:** R15 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2024
- **Award amount:** $98,800
- **Award type:** 3
- **Project period:** 2023-08-01 → 2026-07-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/11009708

## Citation

> US National Institutes of Health, RePORTER application 11009708, Rearrangement Reactions of Divinyldiaziridines for the Enantioselective Synthesis of Diazepines and Benzodiazepines - Supplemental for Equipment Purchase (3R15GM151707-01S1). Retrieved via AI Analytics 2026-05-25 from https://api.ai-analytics.org/grant/nih/11009708. Licensed CC0.

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