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Synthesis
DOI: 10.1055/a-2349-6736
paper

Iodo-Annulations of N-benzyl-propiolamides leading to azaspiro[5.5]- undecatrienones/benzo[c]azepinones

Chada Raji Reddy 
1   Department of Organic Synthesis & Process Chemistry, Indian Institute of Chemical Technology, Hyderabad, India
,
Thallamapuram Nagendraprasad
1   Department of Organic Synthesis & Process Chemistry, Indian Institute of Chemical Technology, Hyderabad, India
,
Jannatul Islam
1   Department of Organic Synthesis & Process Chemistry, Indian Institute of Chemical Technology, Hyderabad, India
,
Uprety Ajaykumar
1   Department of Organic Synthesis & Process Chemistry, Indian Institute of Chemical Technology, Hyderabad, India
,
C. Suresh Reddy
2   Chemistry, S V University, Hyderabad, India
,
Srivari Chandrashekar 
1   Department of Organic Synthesis & Process Chemistry, Indian Institute of Chemical Technology, Hyderabad, India
› Author AffiliationsSupported by: Science and Engineering Research Board CRG/2021/007367
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In this paper, I2-mediated oxidative annulations of N-benzyl-propiolamides has been disclosed for the first time, providing either azaspiro[5.5]undecatrienones via dearomative ipso-annulation or benzo[c]azepinones through ortho-annulation. The selective construction of aforementioned products is based on the ceric ammonium nitrate (CAN)-promoted divergent reactivity of the propiolamide, directed by the substitution on phenyl ring of N-Benzyl group



Publication History

Received: 19 April 2024

Accepted after revision: 20 June 2024

Accepted Manuscript online:
20 June 2024

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