[3 + 2] Cycloadditions with Azirines under the Conditions of Photoinduced Electron Transfer: A New Method for the Synthesis of Imidazoles and Heterophanes | Zendy

Müller Felix | Zendy; Mattay Jochen | Zendy

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[3 + 2] Cycloadditions with Azirines under the Conditions of Photoinduced Electron Transfer: A New Method for the Synthesis of Imidazoles and Heterophanes

Author(s) -

Müller Felix,

Mattay Jochen

Publication year - 1993

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19931260235

Subject(s) - chemistry , synthon , bicyclic molecule , photoinduced electron transfer , azirine , electron transfer , porphyrin , photochemistry , combinatorial chemistry , stereochemistry , organic chemistry , ring (chemistry)

With the opening of azirine rings under the conditions of photoinduced electron transfer a new synthon for the synthesis of heterocycles is available. The formed 2‐azaallenyl radical cation readily reacts with imines to form N 1‐substituted imidazoles in reasonable yields. The synthesis of pyrrolophanes and imidazolophanes from bicyclic azirines is possible as well. With oligocyclic azirines complex heteroaromatic systems and even a porphyrin system can be built up.

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