Seleno/Thio-functionalized ipso-Annulation of N-Propiolyl-2-arylbenzimidazole to Construct Azaspiro[5,5]undecatrienones

Chada Raji Reddy; Ejjirotu Srinivasu; Muppidi Subbarao

doi:10.1021/acs.joc.3c01991

Seleno/Thio-functionalized ipso-Annulation of N-Propiolyl-2-arylbenzimidazole to Construct Azaspiro[5,5]undecatrienones

J Org Chem. 2023 Dec 1;88(23):16485-16496. doi: 10.1021/acs.joc.3c01991. Epub 2023 Nov 9.

Authors

Chada Raji Reddy^{1

2}, Ejjirotu Srinivasu^{1

2}, Muppidi Subbarao^{1

2}

Affiliations

¹ Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
² Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.

PMID: 37943010
DOI: 10.1021/acs.joc.3c01991

Abstract

Till date, the ipso-cyclization of propiolamides is limited to provide azaspiro[4,5]decatrienones. Herein, we present the first example of ipso-carbocyclization, leading to azaspiro[5,5]-undecatrienones from N-propiolyl-2-arylbenzimidazoles, involving both the radical-based and electrophilic reactions. This report establishes an access to a wide range of chalcogenated (SCN/SCF₃/SePh) benzimidazo-fused azaspiro[5,5]undecatrienones in good yields.