Dipole‐Transmissive 1,3‐Dipolar Cycloadditions for the Rapid Construction of Polycyclic N‐Heterocycles: Synthetic and Mechanistic Investigations

Abstract: The investigation of distinctive dipole‐transmissive dipolar cycloaddition (DTDC) methodology and the formalisation of this concept is reported. A DTDC procedure was able to be developed by taking advantage of the structural complementarity of azide and diazoalkane 1,3‐dipoles. Intramolecular azide‐alkene 1,3‐DCs followed by spontaneous dipole transmission upon work‐up furnished intermediate α‐diazoisoindole and α‐diazoisoquinoline substrates bearing the key secondary diazoalkane 1,3‐dipole. N‐Derivatisation of the intermediate α‐diazoisoindole and α‐diazoisoquinolines with a tethered secondary dipolarophile followed by a subsequent 1,3‐DC allowed for rapid construction of a range of functionalised polycyclic N‐heterocycles. Integrated experimental and theoretical studies established requirements for product formation and revealed the likely mechanistic basis of divergent reactivity observed.

Objekt anzeigen

• Standort: Deutsche Nationalbibliothek Frankfurt am Main
• Umfang: Online-Ressource
• Sprache: Englisch

Verweise und Beziehungen

• Erschienen in: Dipole‐Transmissive 1,3‐Dipolar Cycloadditions for the Rapid Construction of Polycyclic N‐Heterocycles: Synthetic and Mechanistic Investigations ; day:16 ; month:06 ; year:2023 ; extent:8 ; Chemistry - a European journal ; (16.06.2023) (gesamt 8)

Beteiligte, Orts- und Zeitangaben

• Urheber: Henneveld, Jackson S. ; Shiri, Farshad ; Ariafard, Alireza ; Lucas, Nigel T. ; Bissember, Alex ; Hawkins, Bill C.

Weitere Informationen

• DOI: 10.1002/chem.202301254
• URN: urn:nbn:de:101:1-2023061615351375760537
• Rechteinformation: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.