Efficient and regioselective synthesis of <i>ortho</i>-diiodinated homobenzylic alcohol derivatives: <i>in silico</i> evaluation as potential anticancer IDO/TDO inhibitors

Al-Zoubi, Raed M.; Al-Jammal, Walid K.; Shkoor, Mohanad; Bani-Yaseen, Abdulilah D.; Khan, Abbas; Agouni, Abdelali; McDonald, Robert

doi:10.1039/d4ob01076k

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob01076k

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Efficient and regioselective synthesis of ortho-diiodinated homobenzylic alcohol derivatives: in silico evaluation as potential anticancer IDO/TDO inhibitors

Raed M. Al-Zoubi,

Walid K. Al-Jammal,

Mohanad Shkoor

et al.

Abstract: A simple and direct synthesis of 2,6-diiodophenylethanol building blocks through highly regioselective metalation (MIE)/oxirane SN2-type ring opening of 1,2,3-triiodobenzene is described. A significant impact of the nature of the R1...

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Microwave‐Assisted/Pd‐Catalyzed Regioselective Double C‐N Arylations of 1,2,3‐Triiodobenzene: Efficient and Unexpected Synthesis of N¹,N²‐Bis(2,3‐diiodoaryl)benzene‐1,2‐diamines

Al‐Zoubi,

Obaidawi,

Al‐Jammal

et al. 2024

Applied Organom Chemis

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A simple, direct, and regioselective protocol to the synthesis of N1,N2‐bis(2,3‐diiodoaryl)benzene‐1,2‐diamines through highly regioselective microwave‐assisted/palladium‐catalyzed double C‐N arylations of 1,2,3‐triiodobenzene and benzene‐1,2‐diamine is reported. Remarkably, the C‐N arylations proceeded bimolecularly at the terminal positions, the most active and less hindered position. This process was efficient and tolerated a wide range of substrates. The reaction of electron‐rich/neutral 1,2,3‐triiodoarene systems and electron‐rich 1,2‐diamines under the optimized conditions provided the highest isolated yields. This article describes a method for the first and unprecedented synthesis of tetra‐iodinated N1,N2‐diarylbenzene‐1,2‐diamine and iodinated 5,10‐dihydrophenazine products that is regioselective and scalable and provides useful derivatives for other chemical reactions especially in the synthesis of new NHC ligands.

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Microwave‐Assisted/Pd‐Catalyzed Regioselective Double C‐N Arylations of 1,2,3‐Triiodobenzene: Efficient and Unexpected Synthesis of N¹,N²‐Bis(2,3‐diiodoaryl)benzene‐1,2‐diamines

Al‐Zoubi,

Obaidawi,

Al‐Jammal

et al. 2024

Applied Organom Chemis

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Efficient and regioselective synthesis of ortho-diiodinated homobenzylic alcohol derivatives: in silico evaluation as potential anticancer IDO/TDO inhibitors

Abstract: A simple and direct synthesis of 2,6-diiodophenylethanol building blocks through highly regioselective metalation (MIE)/oxirane SN2-type ring opening of 1,2,3-triiodobenzene is described. A significant impact of the nature of the R1...

Cited by 1 publication

References 51 publications

Microwave‐Assisted/Pd‐Catalyzed Regioselective Double C‐N Arylations of 1,2,3‐Triiodobenzene: Efficient and Unexpected Synthesis of N¹,N²‐Bis(2,3‐diiodoaryl)benzene‐1,2‐diamines

Microwave‐Assisted/Pd‐Catalyzed Regioselective Double C‐N Arylations of 1,2,3‐Triiodobenzene: Efficient and Unexpected Synthesis of N¹,N²‐Bis(2,3‐diiodoaryl)benzene‐1,2‐diamines

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Efficient and regioselective synthesis of ortho-diiodinated homobenzylic alcohol derivatives: in silico evaluation as potential anticancer IDO/TDO inhibitors

Abstract: A simple and direct synthesis of 2,6-diiodophenylethanol building blocks through highly regioselective metalation (MIE)/oxirane SN2-type ring opening of 1,2,3-triiodobenzene is described. A significant impact of the nature of the R1...

Cited by 1 publication

References 51 publications

Microwave‐Assisted/Pd‐Catalyzed Regioselective Double C‐N Arylations of 1,2,3‐Triiodobenzene: Efficient and Unexpected Synthesis of N1,N2‐Bis(2,3‐diiodoaryl)benzene‐1,2‐diamines

Microwave‐Assisted/Pd‐Catalyzed Regioselective Double C‐N Arylations of 1,2,3‐Triiodobenzene: Efficient and Unexpected Synthesis of N1,N2‐Bis(2,3‐diiodoaryl)benzene‐1,2‐diamines

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Microwave‐Assisted/Pd‐Catalyzed Regioselective Double C‐N Arylations of 1,2,3‐Triiodobenzene: Efficient and Unexpected Synthesis of N¹,N²‐Bis(2,3‐diiodoaryl)benzene‐1,2‐diamines

Microwave‐Assisted/Pd‐Catalyzed Regioselective Double C‐N Arylations of 1,2,3‐Triiodobenzene: Efficient and Unexpected Synthesis of N¹,N²‐Bis(2,3‐diiodoaryl)benzene‐1,2‐diamines