General and cost-effective synthesis of 1-heteroaryl/arylcycloalkylamines and their broad applications

作者：Zhang Dehui; Zheng Hongchao; Wang Xiaodong^*

来源：Tetrahedron, 2016, 72(16): 1941-1953.

DOI：10.1016/j.tet.2016.02.060

• Pyridinylcycloalkylamines
• Arylcycloalkylamines
• Cyclization
• Quaternary carbon center
• One-pot hydrolysis/Curtius rearrangement

A general and cost-effective route has been developed to synthesize 1-heteroarylsubstituted cycloalkylamines from readily available heteroarylacetate in good yields. This synthesis features a LHMDS promoted cyclization and one-pot hydrolysis/Curtius rearrangement. This route can be easily carried out on multi-gram scale and be also used to prepare 1-arylsubstituted cydoallcyl/cycloheteroalkylamines. 1Heteroaryl/arylsubstituted cycloalkyl/cycloheteroalkylamines are versatile building blocks and their applications in organic and medicinal chemistry have been demonstrated in the synthesis of morpholine and N-methylpiperazine analogues and a known Rho kinase inhibitor compound 9.

• 出版日期2016-4-21