Direct Formation of C–C, C–N, and C–O Bonds in Dihydroquinazolines via Hypervalent Iodine(III)-Mediated sp<sup>3</sup> C–H Functionalization

Carlson, Haley M.; Smith, Sydney R.; Mosey, R. Adam

doi:10.1021/acs.joc.3c02334

J. Org. Chem.

2024

DOI: 10.1021/acs.joc.3c02334

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Direct Formation of C–C, C–N, and C–O Bonds in Dihydroquinazolines via Hypervalent Iodine(III)-Mediated sp³ C–H Functionalization

Haley M. Carlson,

Sydney R. Smith,

R. Adam Mosey

Abstract: A hypervalent iodine(III)-mediated cross-dehydrogenative coupling reaction for the direct formation of C−C, C−N, and C−O bonds in dihydroquinazolines has been developed. This one-pot method allows for the synthesis of C4-disubstituted dihydroquinazolines as well as C4-spirolactam, spirolactone, and spiroindene dihydroquinazolines in moderate to high yields.

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Cited by 4 publications

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Iodine Mediated Annulation of Triethylamine, Aldehydes and 2‐Aminopyridines for the Synthesis of 3‐Formyl‐Imidazo [1,2‐a]pyridine Derivatives

Zhang,

Shen,

Zhang

2024

Adv Synth Catal

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With triethylamine as a synthon, an alternative method for the synthesis of 3‐formyl imidazo[1,2‐a]pyridines has been accomplished from aldehydes, and 2‐aminopyridines. The reaction proceeded via iodine‐catalyzed C−N bond cleavage of triethylamine, generation of α,β‐unsaturated aldehyde in situ, and oxidative cyclization with air as the oxygen source. This protocol may facilitate the synthesis of imidazo[1,2‐a]pyridine derivatives and provide a reference for the usage of triethylamine as a synthon.

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Iodine Mediated Annulation of Triethylamine, Aldehydes and 2‐Aminopyridines for the Synthesis of 3‐Formyl‐Imidazo [1,2‐a]pyridine Derivatives

Zhang,

Shen,

Zhang

2024

Adv Synth Catal

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Multicomponent Cross-Dehydrogenative Coupling of Imidazo[1,2-a]pyridine: Access to Abnormal Mannich and Mannich-Type Reaction

Rahaman,

Sahay,

Kumari

et al. 2024

J. Org. Chem.

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This study showcases successfully switchable approaches to accomplish the C3-aryl methylation and C3amino methylation of privileged nitrogen-containing pharmaceutical compounds "imidazopyridines" with distinct amines, which surmounts the long-standing requirement for a superfluous directing group. These two transformations manifest pronounced regio-and chemo-divergent behavior, successfully demonstrating unprecedented multicomponent "abnormal Mannich and Mannichtype" reactions. The remarkable environmentally benign protocol has been efficiently extended to concise the synthesis and late-stage derivatization.

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Constructing new bonds to carbon in dihydroquinazolines via hypervalent iodine(iii)-mediated C(sp³)–C(sp³) bond functionalization

Carlson,

Marshall,

Burton

et al. 2024

Chem. Commun.

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Direct Formation of C–C, C–N, and C–O Bonds in Dihydroquinazolines via Hypervalent Iodine(III)-Mediated sp³ C–H Functionalization

Cited by 4 publications

References 37 publications

Iodine Mediated Annulation of Triethylamine, Aldehydes and 2‐Aminopyridines for the Synthesis of 3‐Formyl‐Imidazo [1,2‐a]pyridine Derivatives

Iodine Mediated Annulation of Triethylamine, Aldehydes and 2‐Aminopyridines for the Synthesis of 3‐Formyl‐Imidazo [1,2‐a]pyridine Derivatives

Multicomponent Cross-Dehydrogenative Coupling of Imidazo[1,2-a]pyridine: Access to Abnormal Mannich and Mannich-Type Reaction

Constructing new bonds to carbon in dihydroquinazolines via hypervalent iodine(iii)-mediated C(sp³)–C(sp³) bond functionalization

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Direct Formation of C–C, C–N, and C–O Bonds in Dihydroquinazolines via Hypervalent Iodine(III)-Mediated sp3 C–H Functionalization

Cited by 4 publications

References 37 publications

Iodine Mediated Annulation of Triethylamine, Aldehydes and 2‐Aminopyridines for the Synthesis of 3‐Formyl‐Imidazo [1,2‐a]pyridine Derivatives

Iodine Mediated Annulation of Triethylamine, Aldehydes and 2‐Aminopyridines for the Synthesis of 3‐Formyl‐Imidazo [1,2‐a]pyridine Derivatives

Multicomponent Cross-Dehydrogenative Coupling of Imidazo[1,2-a]pyridine: Access to Abnormal Mannich and Mannich-Type Reaction

Constructing new bonds to carbon in dihydroquinazolines via hypervalent iodine(iii)-mediated C(sp3)–C(sp3) bond functionalization

Contact Info

Product

Resources

About

Direct Formation of C–C, C–N, and C–O Bonds in Dihydroquinazolines via Hypervalent Iodine(III)-Mediated sp³ C–H Functionalization

Constructing new bonds to carbon in dihydroquinazolines via hypervalent iodine(iii)-mediated C(sp³)–C(sp³) bond functionalization