Fe-Catalyzed Domino Intramolecular Nucleophilic Substitution of 4-Hydroxychromen-2-one and Pyran-2-one/Ring Opening of Activated Arene: An Easy Access to 2,3-Disubstituted Furo[3,2,-c]coumarins and Furo[3,2,-c]pyran-4-ones via Nonsymmetric Triarylmethanes

Wayland E. Noland; Honnaiah Vijay Kumar; Arjun Sharma; Binyuan Wei; Selamawit Girmachew

doi:10.1021/acs.orglett.0c00123

Fe-Catalyzed Domino Intramolecular Nucleophilic Substitution of 4-Hydroxychromen-2-one and Pyran-2-one/Ring Opening of Activated Arene: An Easy Access to 2,3-Disubstituted Furo[3,2,-c]coumarins and Furo[3,2,-c]pyran-4-ones via Nonsymmetric Triarylmethanes

Wayland E. Noland, Honnaiah Vijay Kumar, Arjun Sharma, Binyuan Wei, Selamawit Girmachew

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

A one-pot synthesis of functionalized 2,3-disubstituted furo[3,2,-c]coumarins and furo[3,2,-c]pyran-4-ones under hydrated ferric sulfate catalysis was performed. It was revealed that the reaction proceeds with intramolecular cyclofunctionalization of nonsymmetric triarylmethanes via ring opening of 2-methylfuran followed by recyclization, resulting in the selective formation of desired products. The versatility of this method was demonstrated via the succinct synthesis of an anticoagulant agent analogue and 2,3-disubstituted benzofurans.

Original language	English (US)
Pages (from-to)	1801-1806
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.0c00123
State	Published - Mar 6 2020

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Noland, W. E., Kumar, H. V., Sharma, A., Wei, B., & Girmachew, S. (2020). Fe-Catalyzed Domino Intramolecular Nucleophilic Substitution of 4-Hydroxychromen-2-one and Pyran-2-one/Ring Opening of Activated Arene: An Easy Access to 2,3-Disubstituted Furo[3,2,-c]coumarins and Furo[3,2,-c]pyran-4-ones via Nonsymmetric Triarylmethanes. Organic Letters, 22(5), 1801-1806. https://doi.org/10.1021/acs.orglett.0c00123

Fe-Catalyzed Domino Intramolecular Nucleophilic Substitution of 4-Hydroxychromen-2-one and Pyran-2-one/Ring Opening of Activated Arene : An Easy Access to 2,3-Disubstituted Furo[3,2,-c]coumarins and Furo[3,2,-c]pyran-4-ones via Nonsymmetric Triarylmethanes. / Noland, Wayland E.; Kumar, Honnaiah Vijay; Sharma, Arjun; Wei, Binyuan; Girmachew, Selamawit.

In: Organic Letters, Vol. 22, No. 5, 06.03.2020, p. 1801-1806.

Research output: Contribution to journal › Article › peer-review

Noland, WE, Kumar, HV, Sharma, A, Wei, B & Girmachew, S 2020, 'Fe-Catalyzed Domino Intramolecular Nucleophilic Substitution of 4-Hydroxychromen-2-one and Pyran-2-one/Ring Opening of Activated Arene: An Easy Access to 2,3-Disubstituted Furo[3,2,-c]coumarins and Furo[3,2,-c]pyran-4-ones via Nonsymmetric Triarylmethanes', Organic Letters, vol. 22, no. 5, pp. 1801-1806. https://doi.org/10.1021/acs.orglett.0c00123

Noland WE, Kumar HV, Sharma A, Wei B, Girmachew S. Fe-Catalyzed Domino Intramolecular Nucleophilic Substitution of 4-Hydroxychromen-2-one and Pyran-2-one/Ring Opening of Activated Arene: An Easy Access to 2,3-Disubstituted Furo[3,2,-c]coumarins and Furo[3,2,-c]pyran-4-ones via Nonsymmetric Triarylmethanes. Organic Letters. 2020 Mar 6;22(5):1801-1806. https://doi.org/10.1021/acs.orglett.0c00123

Noland, Wayland E. ; Kumar, Honnaiah Vijay ; Sharma, Arjun ; Wei, Binyuan ; Girmachew, Selamawit. / Fe-Catalyzed Domino Intramolecular Nucleophilic Substitution of 4-Hydroxychromen-2-one and Pyran-2-one/Ring Opening of Activated Arene : An Easy Access to 2,3-Disubstituted Furo[3,2,-c]coumarins and Furo[3,2,-c]pyran-4-ones via Nonsymmetric Triarylmethanes. In: Organic Letters. 2020 ; Vol. 22, No. 5. pp. 1801-1806.

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