Unprecedented TMEDA-Catalyzed Regioselective Decarboalkoxy C-N Bond Formation: A Unified Direct Access to Indolo[2,1-a]isoquinoline and Dibenzopyrrocoline Alkaloids

An unprecedented TMEDA-catalyzed, regioselective, decarboethoxy direct C-N coupling protocol towards the synthesis of dibenzopyrocolines 17a - i and 5,6-dihydroindolo[2,1 a ]isoquinoline 15a - f / 18a-c alkaloids via the identification of N,N,N',N'-tetramethylethylenediamine ( TMEDA ) as a...

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Bibliographic Details
Published in:Chemistry, an Asian journal an Asian journal, 2022-05
Main Authors: Yadav, Lalit, Shyamlal, Bharti Rajesh Kumar, Tiwari, Mohit Kumar, Rahaman T A, Abdul, Sen, Janmejaya, Chaudhary, Sandeep
Format: Article
Language:English
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Summary:An unprecedented TMEDA-catalyzed, regioselective, decarboethoxy direct C-N coupling protocol towards the synthesis of dibenzopyrocolines 17a - i and 5,6-dihydroindolo[2,1 a ]isoquinoline 15a - f / 18a-c alkaloids via the identification of N,N,N',N'-tetramethylethylenediamine ( TMEDA ) as a homogeneous catalyst is reported. The transition-metal-free, TMEDA-catalytic novel protocol is operationally simple and showed a wide range of functional group tolerance and substrate compatibility. The gram-scale application and synthesis of naturally occurring Cryptaustoline (dibenzopyrocoline) alkaloid, further highlights the importance and versatile nature of the developed protocol. This finding also offers a TMEDA-catalyzed direct synthesis of dibenzopyrocolines and substituted 5,6dihydroindolo[2,1 -a ]isoquinoline compounds in a one-pot. The probable reaction pathway involves the free-radical sequential approach via a single electron transfer (SET) mechanism.
ISSN:1861-471X
DOI:10.1002/asia.202200398