Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction

Christopher Hulme; Liang Ma; Joseph J. Romano; George Morton; Sheng Yuh Tang; Marie Pierre Cherrier; Steve Choi; Joseph Salvino; Richard Labaudiniere

doi:10.1016/S0040-4039(00)00053-8

Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction

Christopher Hulme, Liang Ma, Joseph J. Romano, George Morton, Sheng Yuh Tang, Marie Pierre Cherrier, Steve Choi, Joseph Salvino, Richard Labaudiniere

Research output: Contribution to journal › Article › peer-review

74 Scopus citations

Abstract

This communication reveals novel applications of the CO₂/MeOH reagent combination coupled with the UDC (Ugi/DeBOC/Cyclize) strategy. The Ugi five component condensation (5CC) affords carbamate protected amino-amides in good yield. When one of the supporting reagents employed in the Ugi reaction possesses a tethered amino-BOC protected functional group, subsequent acid treatment and proton scavenging results in rapid cyclization to cyclic ureas. Additionally, treatment of the 5CC product with base affords hydantoins in good yield, representing a novel and short approach to this class of molecule.

Original language	English (US)
Pages (from-to)	1889-1893
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	12
DOIs	https://doi.org/10.1016/S0040-4039(00)00053-8
State	Published - Mar 18 2000
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction",

abstract = "This communication reveals novel applications of the CO2/MeOH reagent combination coupled with the UDC (Ugi/DeBOC/Cyclize) strategy. The Ugi five component condensation (5CC) affords carbamate protected amino-amides in good yield. When one of the supporting reagents employed in the Ugi reaction possesses a tethered amino-BOC protected functional group, subsequent acid treatment and proton scavenging results in rapid cyclization to cyclic ureas. Additionally, treatment of the 5CC product with base affords hydantoins in good yield, representing a novel and short approach to this class of molecule.",

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T1 - Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction

AU - Hulme, Christopher

AU - Ma, Liang

AU - Romano, Joseph J.

AU - Morton, George

AU - Tang, Sheng Yuh

AU - Cherrier, Marie Pierre

AU - Choi, Steve

AU - Salvino, Joseph

AU - Labaudiniere, Richard

PY - 2000/3/18

Y1 - 2000/3/18

N2 - This communication reveals novel applications of the CO2/MeOH reagent combination coupled with the UDC (Ugi/DeBOC/Cyclize) strategy. The Ugi five component condensation (5CC) affords carbamate protected amino-amides in good yield. When one of the supporting reagents employed in the Ugi reaction possesses a tethered amino-BOC protected functional group, subsequent acid treatment and proton scavenging results in rapid cyclization to cyclic ureas. Additionally, treatment of the 5CC product with base affords hydantoins in good yield, representing a novel and short approach to this class of molecule.

AB - This communication reveals novel applications of the CO2/MeOH reagent combination coupled with the UDC (Ugi/DeBOC/Cyclize) strategy. The Ugi five component condensation (5CC) affords carbamate protected amino-amides in good yield. When one of the supporting reagents employed in the Ugi reaction possesses a tethered amino-BOC protected functional group, subsequent acid treatment and proton scavenging results in rapid cyclization to cyclic ureas. Additionally, treatment of the 5CC product with base affords hydantoins in good yield, representing a novel and short approach to this class of molecule.

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Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction

Abstract

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