Copper-catalyzed synthesis of medium- and large-sized nitrogen heterocycles via N-arylation of phosphoramidates and carbamates.
[reaction: see text] We have developed an efficient method for the preparation of medium- and large-sized nitrogen heterocycles via copper-catalyzed intramolecular N-arylation of phosphoramidates and carbamates. Introduction of the phosphoryl group or tert-butoxycarbonyl at N-termini can improve intramolecular cyclization under copper catalysis, and the phosphoryl and tert-butoxycarbonyl can easily be removed under the mild conditions; thus, the convenient and efficient method is suitable for the preparation of medium- and large-sized nitrogen heterocycles.
Yang
Ting
T
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, PR China.
Lin
Changxue
C
Fu
Hua
H
Jiang
Yuyang
Y
Zhao
Yufen
Y
D000577:Amides / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry*
D000577:Amides; D001555:Benzene Derivatives; D002219:Carbamates; D006574:Heterocyclic Compounds, 2-Ring; D010756:Phosphoric Acids; D003300:Copper; C011067:phosphoramidic acid; D009584:Nitrogen