One-Pot Synthesis of Pyranocarbazoles by Ethylenediamine Diacetate Catalyzed Domino Aldol-Type Reaction/6 pi-Electrocyclization of Hydroxycarbazoles to alpha,beta-Unsaturated Aldehydes and Conversion into Other Pyranocarbazoles

Title
One-Pot Synthesis of Pyranocarbazoles by Ethylenediamine Diacetate Catalyzed Domino Aldol-Type Reaction/6 pi-Electrocyclization of Hydroxycarbazoles to alpha,beta-Unsaturated Aldehydes and Conversion into Other Pyranocarbazoles
Author(s)
이용록판딧라메쉬월프라사드
Keywords
PYRANOCHALCONE NATURAL-PRODUCTS; ACTIVE CARBAZOLE ALKALOIDS; CONCISE TOTAL-SYNTHESIS; MURRAYA-KOENIGII; EFFICIENT SYNTHESIS; ORIXALONE-D; ROUTE; MAHANIMBINE; LEAVES; TRANS-3,4-DIHYDROXY-3,4-DIHYDROMOLLUGIN
Issue Date
201209
Publisher
GEORG THIEME VERLAG KG
Citation
SYNTHESIS-STUTTGART, v.44, no.18, pp.2910 - 2918
Abstract
A new synthetic route for biologically interesting pyranocarbazoles was developed by reaction of 2- or 4-hydroxycarbazole with alpha,beta-unsaturated aldehydes in the presence of ethylenediamine diacetate (EDDA). The key strategy of this methodology is a formal [3+3] cycloaddition via domino aldol-type/6 pi-electrocyclization. The synthesized pyranocarbazoles can be converted into derivatives bearing substituents on the carbazole and pyran rings.
URI
http://hdl.handle.net/YU.REPOSITORY/27365http://dx.doi.org/10.1055/s-0032-1316766
ISSN
0039-7881
Appears in Collections:
공과대학 > 화학공학부 > Articles
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