Synthesis 2019; 51(18): 3485-3490
DOI: 10.1055/s-0039-1689971
paper
© Georg Thieme Verlag Stuttgart · New York

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

Rail R. Gataullin
a   Ufa Institute of Chemistry of the Russian Academy of Sciences, Prospect Oktyabrya, 71, Ufa 450054, Russian Federation
,
Ekaterina S. Mescheryakova
b   Institute of Petrochemistry and Catalysis of the Russian Academy of Sciences, Prospect Oktyabrya, 141, Ufa 450075, Russian Federation
,
Rifkat M. Sultanov
c   Ufa State Petroleum Technological University, Kosmonavtov str, 1, Ufa 450062, Russian Federation   Email: gataullin@anrb.ru
,
Akhnef A. Fatykhov
a   Ufa Institute of Chemistry of the Russian Academy of Sciences, Prospect Oktyabrya, 71, Ufa 450054, Russian Federation
,
Leonard M. Khalilov
b   Institute of Petrochemistry and Catalysis of the Russian Academy of Sciences, Prospect Oktyabrya, 141, Ufa 450075, Russian Federation
› Author Affiliations
This study was performed in the scope of the "Design, directed synthesis and study of the biological activity of functionalized benzo fused heterocycles, polyheteromono-, bicyclic N,N-, N,O-, S,O-containing systems and uracil derivatives" governmental task (topic no. AAAA-A19-119011790021-4).
Further Information

Publication History

Received: 07 February 2019

Accepted after revision: 14 May 2019

Publication Date:
19 June 2019 (online)


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.

Supporting Information

 
  • References

  • 1 Schaefer GI, Perez JR, Duvall JR, Shamji AF, Schreiber SL. J. Am. Chem. Soc. 2013; 135: 9675
  • 2 Narjes F, Crescenzi B, Ferrara M, Habermann J, Colarusso S, Ferreira M, Stansfield I, Mackay A, Conte I, Ercolani C, Zaramella S, Palumbi M, Meuleman P, Leroux-Roels G, Giuliano C, Fiore F, Di Marco S, Baiocco P, Koch U, Migliaccio G, Altamura S, Laufer R, DeFrancesco R, Rowley M. J. Med. Chem. 2011; 54: 289
  • 3 Miki T, Kori M, Fujishima A, Mabuchi H, Tozawa R, Nakamura M, Sugiyama Y, Yukimasa H. Bioorg. Med. Chem. 2002; 10: 385
  • 4 Mitra S, Banerjee TS, Hota SK, Bhattacharya D, Das S, Chattopadhyay P. Eur. J. Med. Chem. 2011; 46: 1713
  • 5 Mishra JK, Samanta K, Jain M, Dikshit M, Panda G. Bioorg. Med. Chem. Lett. 2010; 20: 244
  • 6 Ransborg LK, Overgaard M, Hejmanowska J, Barfüsser S, Jørgensen KA, Albrecht Ł. Org. Lett. 2014; 16: 4182
  • 7 van Otterlo WA. L, Morgans GL, Khanye SD, Aderibigbe BA. A, Michael JP, Billing DG. Tetrahedron Lett. 2004; 45: 9171
  • 8 Taher A, Aderibigbe BA, Morgans GL. Madeley L. G, Khanye SD, van der Westhuizen L, Fernandes MA, Smith VJ, Michael JP, Green IR, van Otterlo WA. L. Tetrahedron 2013; 69: 2038
  • 9 Dragutan V, Dragutan I. J. Organomet. Chem. 2006; 691: 5129
  • 10 Sahn JJ, Martin SF. Tetrahedron Lett. 2011; 52: 6855
  • 11 Dockendorff C, Faloon PW, Pu J, Yu M, Johnston S, Bennion M, Penman M, Nieland TJ. F, Dandapani S, Perez JR, Munoz B, Palmer MA, Schreiber SL, Krieger M. Bioorg. Med. Chem. Lett. 2015; 25: 2100
  • 12 Jian X, Liu H. Electrophilic Cyclization . In Comprehensive Organic Synthesis, 2nd ed., Part 1, Vol. 4. Knochel P, Molander GA, Johnson J. Elsevier; Amsterdam: 2014: 412-465
  • 13 Dowle MD, Davies DI. Chem. Soc. Rev. 1979; 8: 171
  • 14 Liu H, Pan Y, Tan C.-H. Tetrahedron Lett. 2008; 49: 4424
  • 15 Agejas J, Delgado F, Vaquero JJ, García-Navío JL, Lamas C. Tetrahedron Lett. 2002; 43: 8025
  • 16 Mazgarova GG, Fatykhov AA, Gataullin RR. Russ. J. Org. Chem. 2014; 50: 1155
  • 17 Gataullin RR, Ishberdina RR, Kazhanova TV, Shitikova OV, Spirikhin LV, Abdrakhmanov IB. Mendeleev Commun. 2004; 14: 219
  • 18 Gataullin RR, Ishberdina RR, Shitikova OV, Minnigulov FF, Spirikhin LV, Abdrakhmanov IB. Chem. Heterocycl. Compd. 2006; 42: 1025
  • 19 Gataullin RR, Ibatullina ZA, Mesherjakova ES, Fatykhov AA, Khalilov LM. Russ. J. Org. Chem. 2017; 53: 697
  • 20 Bizhanova GG, Suponitskii KYu, Vakhitova JV, Gataullin RR. Tetrahedron 2017; 73: 109
  • 21 Cadogan JI. G, Cameron DK, Gosney I, Highcock RM, Newlands SF. J. Chem. Soc., Chem. Commun. 1986; 766
  • 22 Gataullin RR, Suponitsky KYu. Mendeleev Commun. 2009; 19: 284
  • 23 Gataullin RR, Sotnikov AM, Spirikhin LV, Abdrakhmanov IB. Russ. J. Org. Chem. 2005; 41: 715
  • 24 CCDC 1828958 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
  • 25 CrysAlis Pro. Agilent Technologies; Yarnton (Oxfordshire, UK): 2012
  • 26 OLEX2: Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JA. K, Puschmann H. J. Appl. Cryst. 2009; 42: 339
  • 27 Sheldrick GM. A. Acta Cryst. 2008; A64: 112
  • 28 Mercury: Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M, van de Streek J. J. Appl. Cryst. 2006; 39: 453