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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.