An Unexpected Dihalogenation/Dehydrogenation Product Derived­ via Iodolactonization of an N-Tosyl-N-[6-(2-cyclopenten-1-yl)-2-methylphenyl]glycine

Rail R. Gataullin; Ekaterina S. Mescheryakova; Rifkat M. Sultanov; Akhnef A. Fatykhov; Leonard M. Khalilov

doi:10.1055/s-0039-1689971

Synthesis, Table of Contents

Synthesis 2019; 51(18): 3485-3490
DOI: 10.1055/s-0039-1689971

paper

An Unexpected Dihalogenation/Dehydrogenation Product Derived via Iodolactonization of an N-Tosyl-N-[6-(2-cyclopenten-1-yl)-2-methylphenyl]glycine

Rail R. Gataullin∗

^aUfa Institute of Chemistry of the Russian Academy of Sciences, Prospect Oktyabrya, 71, Ufa 450054, Russian Federation

,

Ekaterina S. Mescheryakova

^bInstitute of Petrochemistry and Catalysis of the Russian Academy of Sciences, Prospect Oktyabrya, 141, Ufa 450075, Russian Federation

,

Rifkat M. Sultanov

^cUfa State Petroleum Technological University, Kosmonavtov str, 1, Ufa 450062, Russian Federation Email: gataullin@anrb.ru

,

Akhnef A. Fatykhov

^aUfa Institute of Chemistry of the Russian Academy of Sciences, Prospect Oktyabrya, 71, Ufa 450054, Russian Federation

,

Leonard M. Khalilov

^bInstitute of Petrochemistry and Catalysis of the Russian Academy of Sciences, Prospect Oktyabrya, 141, Ufa 450075, Russian Federation

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Abstract

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Abstract

The reaction between N-tosyl-N-[6-(2-cyclopenten-1-yl)phenyl]glycine (syn/anti atropisomeric mixture) and molecular iodine is studied. Along with the expected 8-exo-cyclization product possessing a 3-iodo-2,3,3a,6,7,11b-hexahydrobenzo[e]cyclopenta[g][1,4]oxazocine core, the unexpected 1,11b-dehydrogenated/1-iodinated analogue with a 1,3-diiodo-3,3a,6,7-tetrahydrobenzo[e]cyclopenta[g][1,4]oxazocine structure is observed for the first time in a conventional halolactonization reaction.

Key words

benzoxazepines - halolactonization - atropisomers - glycine - X-ray crystal structure analysis

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References

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Supplementary Material

Supporting Information

An Unexpected Dihalogenation/Dehydrogenation Product Derived­ via Iodolactonization of an N-Tosyl-N-[6-(2-cyclopenten-1-yl)-2-methylphenyl]glycine

An Unexpected Dihalogenation/Dehydrogenation Product Derived via Iodolactonization of an N-Tosyl-N-[6-(2-cyclopenten-1-yl)-2-methylphenyl]glycine