Ring Opening of Donor–Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N‐Heterocycles

Abstract

What is the most significant result of this study?The regioselective and stereospecific ring opening of donor-acceptor cyclopropanes with the azide ion allows for the construction of valuable building blocks, in racemic as well as optically active forms, densely decorated with different functional groups. Impressive variability and good tolerance of these functionalities, on the one hand, combined with their strategic placement and their ability to undergo selective modification, on the other hand, opens a straightforward route to a plethora of N-heterocycles of high synthetic and biological relevance. In our research, a broad skeletal array of five-, six-, and seven-membered N-heterocyclic systems, involving pyrrole, pyridine, azepine, triazole, and tetrazole cores, was obtained from simple synthetic operations starting from the synthesized azide building blocks. What was the inspiration for this cover design?One of the main aims of this research was to create numerous synthetic opportunities and to achieve diverse synthetic outcomes by using different combinations of the same parent compounds. To us, this image of a simple yet exciting kaleidoscope provides a splendid visual metaphor for this approach: a primitive rotating tube which keeps on giving us new combinations of coloured pieces of glass and, therefore, delights us with unforgettable pictures. What future opportunities do you see?We predict that the future opportunities will rely on the development of synthetic sequences for combinatorial, diversity-, or biology-oriented synthesis in drug discovery efforts due to an impressive synthetic potential of these building blocks. Evidently, this potential is not restricted to the set of transformations developed in the present study and can spread far beyond its boundaries.Invited for the cover of this issue is the group of Ekaterina M. Budynina and Igor V. Trushkov at Lomonosov Moscow State University. The image depicts the diversity of synthetic outcomes that can be achieved by using the ring-opening of donoracceptor cyclopropanes with the azide ion as a triggering reaction. Read the full text of the article at