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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Synthesis of New C2-Symmetric Chiral Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons

Author(s): İrfan Çapan and Süleyman Servi*

Volume 17, Issue 10, 2020

Page: [801 - 805] Pages: 5

DOI: 10.2174/1570178616666190731105327

Price: $65

Abstract

Racemic dicarboxylic acids were synthesized from the Diels-Alder cycloaddition reactions which formed the dibenzobarrelene and norbornene skeletons. The pure enantiomers of these compounds were obtained using brucine as the chiral auxiliary. Novel C2-symmetric chiral benzimidazole derivatives were synthesized from the reaction of the diaminobenzene and enantiomeric dicarboxylic acids in the presence of boric acid.

Keywords: Norbornene, dibenzobarrelene, guanidine, benzimidazole, chiral resolution.

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[1]
Largeron, M.; Nguyen, K. Synthesis, 2018, 50, 241-253.
[http://dx.doi.org/10.1055/s-0036-1590915]
[2]
Ajani, O.O.; Aderohunmu, D.V.; Ikpo, C.O.; Adedapo, A.E.; Olanrewaju, I.O. Arch. Pharm. Chem. Life Sci., 2016, 349, 475-506.
[http://dx.doi.org/10.1002/ardp.201500464]
[3]
Çevik, U.A.; Sağlık, B.N.; Özkay, Y.; Cantürk, Z.; Bueno, J.; Demirci, F.; Koparal, A.S. Curr. Pharm. Des., 2017, 23(15), 2276-2286.
[http://dx.doi.org/10.2174/1381612822666161201150131] [PMID: 27908268]
[4]
Singla, P.; Luxami, V.; Paul, K. RSC Advances, 2014, 4, 12422-12440.
[http://dx.doi.org/10.1039/c3ra46304d]
[5]
Khose, V.N.; John, M.E.; Pandey, A.D.; Karnik, A.V. Tetrahedron Asymmetry, 2017, 28, 1233-1289.
[http://dx.doi.org/10.1016/j.tetasy.2017.09.001]
[6]
Maiti, D.K.; Halder, S.; Pandit, P.; Chatterjee, N.; De Joarder, D.; Pramanik, N.; Saima, Y.; Patra, A.; Maiti, P.K. J. Org. Chem., 2009, 74(21), 8086-8097.
[http://dx.doi.org/10.1021/jo901458k] [PMID: 19799443]
[7]
Balboni, G.; Fiorini, S.; Baldisserotto, A.; Trapella, C.; Sasaki, Y.; Ambo, A.; Marczak, E.D.; Lazarus, L.H.; Salvadori, S. J. Med. Chem., 2008, 51(16), 5109-5117.
[http://dx.doi.org/10.1021/jm800587e] [PMID: 18680274]
[8]
Nájera, C.; Yus, M. Tet. Lett., 2015, 56, 2623-2633.
[http://dx.doi.org/10.1016/j.tetlet.2015.03.099]
[9]
Benavent, L.; Puccetti, F.; Baeza, A.; Gómez-Martínez, M. Molecules, 2017, 22, 1333-1344.
[http://dx.doi.org/10.3390/molecules22081333]
[10]
Tawde, T.S.; Wagh, S.J.; Sapre, J.V.; Khose, V.N.; Badani, P.M.; Karnik, A.V. Tetrahedron Asymmetry, 2016, 27, 130-135.
[http://dx.doi.org/10.1016/j.tetasy.2016.01.002]
[11]
Çapan, I.; Servi, S. ARKIVOC, 2018, 7, 131-142.
[http://dx.doi.org/10.24820/ark.5550190.p010.654]
[12]
Passarello, M.; Abbate, S.; Longhi, G.; Lepri, S.; Ruzziconi, R.; Nicu, V.P. J. Phys. Chem. A, 2014, 118(24), 4339-4350.
[http://dx.doi.org/10.1021/jp502544v] [PMID: 24840313]
[13]
Ramanathan, C.R.; Periasamy, M. Tetrahedron Asymmetry, 1998, 9, 2651-2656.
[http://dx.doi.org/10.1016/S0957-4166(98)00274-2]
[14]
Kanoh, S.; Hongoh, Y.; Motoi, M.; Suda, M. Bull. Chem. Soc. Jpn., 1988, 61, 1032-1034.
[http://dx.doi.org/10.1246/bcsj.61.1032]
[15]
Takacs, J.M.; Quincy, D.A.; Shay, W.; Jones, B.E.; Ross, C.R. Tetrahedron Asymmetry, 1997, 8, 3079-3087.
[http://dx.doi.org/10.1016/S0957-4166(97)00323-6]
[16]
Allenmark, S.; Skogsberg, U.; Thunberg, L. Tetrahedron Asymmetry, 2000, 11, 3527-3534.
[http://dx.doi.org/10.1016/S0957-4166(00)00331-1]
[17]
Maraš, N.; Kočevar, M. Helv. Chim. Acta, 2011, 94, 1860-1874.
[http://dx.doi.org/10.1002/hlca.201100064]

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