Yissum - Research Development Company of the Hebrew University

Synthesis of Heterocycles via Controlled Cyclization of Alpha-Enaminones

Posted by Yissum - Research Development Company of the Hebrew UniversityResponsive · Innovative Products and Technologies · Israel

Summary of the technology

Synthesis of Heterocycles via Controlled Cyclization of Alpha-Enaminones
Project ID : 6-2016-4351

Yissum - Research Development Company of the Hebrew University
Yissum - Research Development Company of the Hebrew University

Description of the technology

Category

Chemistry&Materials

Keywords

α-enaminone, heterocycles, cyclization

Current development stage

General list: TRL2Technology Concept Formulated

Application

  • Oxazine, azaspirone, quinolines, quinolinone, and quinolinol structures are frequently observed as scaffold segments in various biochemical compounds. These architectures have been identified as building blocks of a numerous alkaloids and often remotely related metabolites.
  • Unfortunately, access to a large number of these target molecules, and their structural analogues, is either unknown or hindered by the multistep syntheses.
  • An in-depth analysis of the introduced cores suggests that α-enaminone scaffold of Type-1 has the potential to serve as an operational, collective key unit for their construction via controlled intramolecular cyclizations.
  • However, little is known about α-enaminones, apparently because they are often not directly accessible from the corresponding diketones. Furthermore, methods for the preparation of heterocycles using α-ketoenamines are limited.

Our Innovation

A novel methodology for the synthesis of heterocycles via controlled cyclization of an easily accessible α -Enaminones common key precursors

  • Linking simple and single enaminone core with a diverse, heterocyclic architectures.
  • Unexplored, stable α-enaminone synthones, radically different from other known α- or β-counterparts by their chemical behavior.
  • Unlock unusual functionalities of -enaminone synthones.
  • Accurate design of the starting material allows specific and selective functionalization reactions across the unsaturated scaffold, enabling the preparation of diverse products.

Research Highlights

  • α-enaminones can react as enamines (nucleophiles), as well as α,β-unsaturated ketones (electrophiles).
  • Our finding uncovers unprecedented reactivity of α,β-unsaturated enaminones driven by their “dual electronic attitude”
  • The feasibility of this new concept is demonstrated in the direct functionalization of enaminone precursors, such as alkylation; 1,2- 1,3-, or 1,4-addition; and C−O bond formation.
  • It was successfully demonstrated that readily available α-enaminone precursors undergo facile cyclizations under basic conditions to afford a broad spectrum of heterocycles, such as azaspirones, quinolinones, quinolines, quinolinols, and oxazines.

Fig.1 : New α- enaminone synthone

Fig.2 : Dual electronic attitude of α- enaminone

Opportunity

  • Collective synthesis of several important classes of heterocycles.
  • A potential application for the construction of highly complex systems.
  • Paves the way for novel retrosynthetic pathways in the field of chemical research.

Project manager

Shani Bullock
VP, Business Development, Healthcare

Project researchers

Dmitry Tsvelikhovsky
HUJI, School of Medicine - IMRIC
School of Pharmacy- Institute for Drug Research

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About Yissum - Research Development Company of the Hebrew University

Technology Transfer Office from Israel

Yissum Research Development Company of the Hebrew University of Jerusalem Ltd. Founded in 1964 to protect and commercialize the Hebrew University’s intellectual property. Ranked among the top technology transfer companies, Yissum has registered over 8,900 patents covering 2,500 inventions; has licensed out 800 technologies and has spun-off 90 companies. Products that are based on Hebrew University technologies and were commercialized by Yissum generate today over $2 Billion in annual sales.

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