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

|View full text |Cite

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.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article4

Relationship

Self Cite0

Independent4

Authors

Journals

Cited by 4 publications

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

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

View full text Add to dashboard Cite

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.

show abstract

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

View full text Add to dashboard Cite

show abstract

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.

View full text Add to dashboard Cite

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.

show abstract

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.

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

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

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