A Domino Heck Coupling–Cyclization–Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines

Satyanarayana, G. and Sreenivasulu, Chinnabattigalla and Ghora, Santanu (2022) A Domino Heck Coupling–Cyclization–Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines. Synthesis, 54 (02). pp. 393-402. ISSN 0039-7881

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An efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence. Notably, this protocol occurs in water as a green solvent. Significantly, the method exhibits broad substrate scope and is applied for the synthesis of deuterated quinolines through a deuterium-exchange process. © 2021. Thieme. All rights reserved.

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IITH Creators:
IITH CreatorsORCiD
Satyanarayana, G.UNSPECIFIED
Item Type: Article
Additional Information: We are grateful to the Department of Science and Technology, Science and Engineering Research Board (DST-SERB), New Delhi (Grant No. EMR/2017/005312) for financial support. C.B.S. thanks the University Grants Commission (UGC), India, for the award of a research fellowship. ScienceandEngineeingReeachBoad(EMR/2017005312UnivesiytGansCommission
Uncontrolled Keywords: deuterated quinolines; Heck coupling; iodoanilines; palladium catalysis; quinolines
Subjects: Chemistry
Divisions: Department of Chemistry
Depositing User: . LibTrainee 2021
Date Deposited: 29 Jul 2022 04:25
Last Modified: 29 Jul 2022 04:25
URI: http://raiith.iith.ac.in/id/eprint/10004
Publisher URL: http://doi.org/10.1055/a-1589-7548
OA policy: https://v2.sherpa.ac.uk/id/publication/10869
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