PIFA-BF3·OEt2 mediated intramolecular regioselective domino cyclization of ynamides: A novel method for the synthesis of tetrahydroisoquinoline-oxazol-2(3H)-ones

Winai Ieawsuwan; Somsak Ruchirawat

doi:10.1016/j.bmc.2017.03.034

PIFA-BF₃·OEt₂ mediated intramolecular regioselective domino cyclization of ynamides: A novel method for the synthesis of tetrahydroisoquinoline-oxazol-2(3H)-ones

Bioorg Med Chem. 2017 Jun 1;25(11):2856-2867. doi: 10.1016/j.bmc.2017.03.034. Epub 2017 Mar 19.

Authors

Winai Ieawsuwan¹, Somsak Ruchirawat²

Affiliations

¹ Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand. Electronic address: winai@cri.or.th.
² Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand; Chemical Biology Program, Chulabhorn Graduate Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand; Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand.

PMID: 28351608
DOI: 10.1016/j.bmc.2017.03.034

Abstract

The transition metal-free intramolecular regioselective domino cyclization of N-Boc protected ynamides has been developed to provide the corresponding tetrahydroisoquinoline-oxazo-2(3H)-ones in moderate to good yields.

Keywords: Domino cyclization; Hypervalent iodine; Oxazol-2(3H)-one; Tetrahydroisoquinoline; Ynamide.

MeSH terms

Acetates / chemistry*
Alkynes / chemistry*
Amides / chemistry*
Boranes / chemistry
Cyclization
Ether / chemistry
Iodobenzenes / chemistry*
Isoquinolines / chemical synthesis*
Isoquinolines / chemistry
Molecular Structure
Oxazoles / chemical synthesis*
Oxazoles / chemistry
Stereoisomerism

Substances

Acetates
Alkynes
Amides
Boranes
Iodobenzenes
Isoquinolines
Oxazoles
Ether
(bis(trifluoroacetoxy)iodo)benzene
boron trifluoride