Synlett
DOI: 10.1055/a-2599-1277
letter
Emerging Trends in Organic Chemistry: A Focus on India

Palladium(II)-Catalyzed Alkyne Annulation Reactions for the Synthesis of Cyclopenta[b]naphthalene-1,4-diones

Somadrita Borthakur
a   Applied Organic Chemistry, Chemical Sciences and Technology Division, CSIR-North East Institute of Science and Technology, Jorhat-785006, Assam, India
d   Department of Chemistry, Gauhati University, Gauhati-781014, Assam, India
,
Supriya Khundrakpam
a   Applied Organic Chemistry, Chemical Sciences and Technology Division, CSIR-North East Institute of Science and Technology, Jorhat-785006, Assam, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, Uttar Pradesh, India
,
Sumi Changmai
a   Applied Organic Chemistry, Chemical Sciences and Technology Division, CSIR-North East Institute of Science and Technology, Jorhat-785006, Assam, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, Uttar Pradesh, India
,
Bipul Sarma
c   Department of Chemical Sciences, Tezpur University, Tezpur-784028, Assam, India
,
Dilip Kakati
d   Department of Chemistry, Gauhati University, Gauhati-781014, Assam, India
,
Sanjib Gogoi
a   Applied Organic Chemistry, Chemical Sciences and Technology Division, CSIR-North East Institute of Science and Technology, Jorhat-785006, Assam, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, Uttar Pradesh, India
› Author Affiliations

The authors thank SERB and CSIR, New Delhi, for financially supporting us through the GPP-0367 (CRG/2019/00l898), HCP 049, HCP 050, and OLP 2084 projects.


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Abstract

A palladium-catalyzed C–H activation and alkyne annulation reaction of 2-hydroxy-3-(2-thienyl)naphthalene-1,4-diones has been developed for the construction of biologically important cyclopenta[b]naphthalene-1,4-dione derivatives. This reaction proceeds through hydroxy-group-directed heteroaryl C(sp2)–H activation, insertion of two molecules of an alkyne, and dehydrative cyclization pathways.

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Publication History

Received: 27 February 2025

Accepted after revision: 02 May 2025

Accepted Manuscript online:
02 May 2025

Article published online:
13 June 2025

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