Catalytic amination of 2-substituted pyridines with hydrazine derivatives

J B Arterburn; K V Rao; R Ramdas; B R Dible

doi:10.1021/ol015731y

Catalytic amination of 2-substituted pyridines with hydrazine derivatives

Org Lett. 2001 May 3;3(9):1351-4. doi: 10.1021/ol015731y.

Authors

J B Arterburn¹, K V Rao, R Ramdas, B R Dible

Affiliation

¹ Department of Chemistry and Biochemistry, MSC 3C, New Mexico State University, P.O. Box 30001, Las Cruces, New Mexico 88003, USA. jarterbu@nmsu.edu

PMID: 11348232
DOI: 10.1021/ol015731y

Abstract

[reaction in text] Protected pyridylhydrazine derivatives were prepared in a one-step palladium-catalyzed amination reaction using chelating phosphine ligands. 2-Pyridyl chlorides, bromides, and triflates were effective electrophiles in these reactions. Di-tert-butyl hydrazodiformate was an excellent hydrazine substrate, and the resulting products were deprotected under mild conditions. Catalytic amination provides a direct route to protected bifunctional hydrazinopyridine linkers that are suitable for metal-bioconjugate syntheses.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Amination
Catalysis
Chelating Agents / chemistry
Hydrazines / chemical synthesis
Hydrazines / chemistry*
Molecular Structure
Organometallic Compounds / chemistry
Palladium / chemistry
Pyridines / chemical synthesis
Pyridines / chemistry*
Structure-Activity Relationship

Substances

Chelating Agents
Hydrazines
Organometallic Compounds
Pyridines
Palladium

Grants and funding

GM 08136-26/GM/NIGMS NIH HHS/United States