Synthesis of furan-fused 1,4-dihydrocarbazoles via an unusual Garratt-Braverman Cyclization of indolyl propargyl ethers and their antifungal activity

Mandal, Arundhoti ; Mandal, Santi M. ; Jana, Saibal ; Bag, Subhendu Sekhar ; Das, Amit K. ; Basak, Amit (2018) Synthesis of furan-fused 1,4-dihydrocarbazoles via an unusual Garratt-Braverman Cyclization of indolyl propargyl ethers and their antifungal activity Tetrahedron, 74 (27). pp. 3543-3556. ISSN 0040-4020

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Official URL: http://doi.org/10.1016/J.Tet.2018.05.001

Related URL: http://dx.doi.org/10.1016/J.Tet.2018.05.001

Abstract

The reactivity of indole based bis-propargyl ethers 4a-4g under Garratt-Braverman condition (KOBut in refluxing toluene) has been studied. Interestingly, these propargyl systems with one arm attached with substituted 3-indolyl derivatives leaving the other arm unsubstituted produced the 3,4-furan fused dihydrocarbazole derivatives 6a-6g (and not the expected carbazole derivatives) as the predominant product (70–82%) making this methodology to access such derivatives an attractive route. The results are supported by computational studies and some of the carbazole derivatives showed good antifungal activities.

Item Type:Article
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ID Code:130054
Deposited On:02 Dec 2022 06:00
Last Modified:05 Dec 2022 05:47

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