Ring‐Rearrangement Metathesis of 7‐Azanorbornenes as an Entry to 1‐Azabicyclo[ n .3.0]alkenones | Zendy

Rojas Víctor | Zendy; Carreras Javier | Zendy; Avenoza Alberto | Zendy; Busto Jesús H. | Zendy; Peregrina Jesús M. | Zendy

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Ring‐Rearrangement Metathesis of 7‐Azanorbornenes as an Entry to 1‐Azabicyclo[ n .3.0]alkenones

Author(s) -

Rojas Víctor,

Carreras Javier,

Avenoza Alberto,

Busto Jesús H.,

Peregrina Jesús M.

Publication year - 2013

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201300126

Subject(s) - azepine , chemistry , metathesis , ring closing metathesis , stereochemistry , salt metathesis reaction , ring (chemistry) , pyrrolizidine , indolizidine , cope rearrangement , olefin metathesis , organic chemistry , alkaloid , polymerization , polymer

Pyrrolizidine, indolizidine, and pyrrolo[1,2‐ a ]azepine substructures are present in a large number of naturally occurring azabicyclic compounds, which are currently of special interest because of their biological activities. To obtain this class of compounds, we envisioned a ring‐rearrangement metathesis (RRM) process of 7‐azanorbornene systems that incorporates several exocyclic olefin patterns at the nitrogen position. By using this methodology, we have synthesized a set of new 1‐azabicyclo[ n .3.0]alkenones, which include derivatives of pyrrolam. In all cases, only one regioisomer was obtained. Moreover, new spiro compounds with tricyclic structures have been synthesized by using a domino metathesis process that involves a ring‐opening/ring‐closing/ring‐closing metathesis (ROM/RCM/RCM) sequence.

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