Tandem Nenitzescu reaction/nucleophilic aromatic substitution to form novel pyrido fused indole frameworks

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dc.contributor.author Singh, Rashmi
dc.contributor.author Bhatia, Harshita
dc.contributor.author Prakash, Prabhat
dc.contributor.author Debroye, Elke
dc.contributor.author Dey, Swapan
dc.contributor.author Dehaen, Wim
dc.coverage.spatial United States of America
dc.date.accessioned 2021-10-01T11:45:55Z
dc.date.available 2021-10-01T11:45:55Z
dc.date.issued 2021-09
dc.identifier.citation Singh, Rashmi; Bhatia, Harshita; Prakash, Prabhat; Debroye, Elke; Dey, Swapan and Dehaen, Wim, "Tandem Nenitzescu reaction/nucleophilic aromatic substitution to form novel pyrido fused indole frameworks", European Journal of Organic Chemistry, DOI: 10.1002/ejoc.202100827, vol. 2021, no. 34, pp. 4865-4875, Sep. 2021. en_US
dc.identifier.issn 1434-193X
dc.identifier.issn 1099-0690
dc.identifier.uri https://doi.org/10.1002/ejoc.202100827
dc.identifier.uri https://repository.iitgn.ac.in/handle/123456789/6937
dc.description.abstract Two regioisomeric sets of 5-hydroxy indoles, prepared from Nenitzescu reaction, were transformed to polyfused ring system bearing pyridine, furan and additionally indole as key component through intramolecular nucleophilic substitution. This methodology provides simple access to various linear and angular-shaped pyrido (furo) fused indole frameworks from easily available precursors under mild reaction conditions. 5-Hydroxyindoles are privileged structures that form part of various bioactive compounds. The Nenitzescu reaction of quinones and enamines is one of the most powerful methods to obtain 5-hydroxyindoles. In this work, we have applied the Nenitzescu reaction to 2-(2-chloropyrid-3-yl)benzoquinones. Mixtures of regioisomers were obtained that could be separated in the 4- and 6-substituted analogues, and then cyclized separately in a metal-free base-catalyzed reaction, affording novel tetracyclic indole derivatives. These are indeed the first examples reported in the literature of the linear pyrido[3?,2??:?4,5]furo[3,2-b]indole and angular 1H-pyrido[2?,3??:?4,5]furo[2,3-c]indole systems. The regioselectivity and the yield of the Nenitzescu reaction were found to be dependent on the N-substituent at the enamine. Furthermore, we analyzed the UV-Vis and PL spectra of the new systems, and this was supported by DFT calculations, allowing us to compare the properties of angular compared to linearly shaped compounds.
dc.description.statementofresponsibility by Rashmi Singh, Harshita Bhatia, Dr. Prabhat Prakash, Dr. Elke Debroye, Dr. Swapan Dey and Prof. Wim Dehaen
dc.format.extent vol. 2021, no. 34, pp. 4865-4875
dc.language.iso en_US en_US
dc.publisher Wiley en_US
dc.subject Tandem Nenitzescu Reaction en_US
dc.subject Nucleophilic Aromatic Substitution en_US
dc.subject 5-hydroxy indoles en_US
dc.subject Nenitzescu reaction en_US
dc.subject 2-(2-chloropyrid-3-yl)benzoquinones en_US
dc.title Tandem Nenitzescu reaction/nucleophilic aromatic substitution to form novel pyrido fused indole frameworks en_US
dc.type Article en_US
dc.relation.journal European Journal of Organic Chemistry

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