Formal [4 + 2] benzannulation of 2-alkenyl indoles with aldehydes: a route to structurally diverse carbazoles and bis-carbazoles

Construction of structurally diverse carbazoles and bis-carbazoles by protecting-group-free formal [4 + 2]-benzannulation of 2-alkenyl indoles and aldehydes is demonstrated. The sequence of four different reactions is executed in one-pot using readily available and cheap bottle reagents as catalysts...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-02, Vol.17 (7), p.1822-1826
Main Authors: Banerjee, Ankush, Guin, Avishek, Saha, Shuvendu, Mondal, Anushree, Maji, Modhu Sudan
Format: Article
Language:English
Subjects:
Aldehydes
Carbazoles
Catalysts
Functional groups
Indoles
NMR
Nuclear magnetic resonance
Oxygen
Reagents
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Summary:Construction of structurally diverse carbazoles and bis-carbazoles by protecting-group-free formal [4 + 2]-benzannulation of 2-alkenyl indoles and aldehydes is demonstrated. The sequence of four different reactions is executed in one-pot using readily available and cheap bottle reagents as catalysts rendering this method attractive. The incorporation of inexpensive and environmentally benign molecular oxygen as the oxidant into the final aromatization step enables tolerance of several functional groups. Construction of structurally diverse carbazoles and bis-carbazoles by protecting-group-free formal [4 + 2]-benzannulation of 2-alkenyl indoles and aldehydes is demonstrated.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02875c