Synthesis, Table of Contents Synthesis 2024; 56(19): 3037-3044DOI: 10.1055/a-2349-6736 paper Iodo-Annulations of N-Benzyl-propiolamides Leading To Azaspiro[5.5]undecatrienones or Benzo[c]azepinones Chada Raji Reddy ∗ a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India , Thallamapuram Nagendraprasad a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India b Department of Chemistry, Sri Venkateswara University, Tirupati 517502, Andhra Pradesh, India , Jannatul Islam a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India , Uprety Ajaykumar a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India , Cirandur Suresh Reddy b Department of Chemistry, Sri Venkateswara University, Tirupati 517502, Andhra Pradesh, India , Srivari Chandrasekhar ∗ a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract Iodine-mediated oxidative annulations of N-benzyl-propiolamides are 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 the aforementioned products is based on the ceric ammonium nitrate (CAN)-promoted divergent reactivity of the propiolamide, directed by the substituents on the phenyl ring of the N-benzyl group. Key words Key words ipso-annulation - ceric ammonium nitrate - propiolamide - dearomatization - aza-spirocycle - benzo-azepinone Full Text References References For selected reviews, see: 1a Hiesinger K, Dar’in D, Proschak E, Krasavin M. J. Med. Chem. 2021; 64: 150 1b Lepovitz LT, Martin SF. Tetrahedron 2019; 75: 130637 1c Chupakhin E, Babich O, Prosekov A, Asyakina L, Krasavin M. Molecules 2019; 24: 4165 1d Zheng Y.-J, Tice CM. Expert Opin. Drug Discovery 2016; 11: 831 1e Marson CM. Chem. Soc. Rev. 2011; 40: 5514 For representative reviews, see: 2a Heravi MM, Zadsirjan V. RSC Adv. 2020; 10: 44247 2b Kerru N, Gummidi L, Maddila S, Gangu KK, Jonnalagadda SB. Molecules 2020; 25: 1909 2c Vitaku E, Smith DT, Njardarson JT. J. Med. 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