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

Authors

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

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

Full Text

References

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

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

Authors

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