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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Aza-Darzens Type Reaction of Azirines: Access to Highly Substituted 1-Azabicyclo[1.1.0]butanes and Azetidines
Siruvuri Krishnam Raju1,2, Vankudoth Renuka1,2, Jagadeesh Babu Nanubolu3
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (IICT), Hyderabad, Telangana 500007, India.
Abstract:
A streamlined approach was developed for accessing 2,3,4-substituted 1-azabicyclo[1.1.0]butanes from azirines under aza-Darzens-type reaction conditions. The pronounced ring strain in these bicyclic systems enabled distinctive electrophilic transformations via activation of the N-C(3) bond, leading to the formation of substituted azetidines. The relative configurations of the 1-azabicyclo[1.1.0]butanes were established by 2D NMR, while single-crystal X-ray analysis of the azetidines confirmed their structures and, by analogy, supported the configurational assignments of both these synthesized classes.
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