Subscribe to RSS
DOI: 10.1055/a-2047-6742
Polycyclic High-Density Cage Compounds via Cross Metathesis
Defense Research and Development Organisation (DRDO, NO. ARDB/01/1041849/M/1), New Delhi-India.
Abstract
The synthesis of various highly functionalized caged systems suitable as high energy density materials, which were assembled by utilization of an olefin cross-metathesis strategy, is reported. E-Selectivity was observed during the cross-metathesis by using Grubbs second generation catalyst (G-II) and N-tolyl Grubbs catalyst in most of the cross-metathesis products. The stereochemistry of the olefin formed during the cross-metathesis has been determined unambiguously by a single-crystal X-ray diffraction study.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2047-6742.
- Supporting Information
- CIF File
Publication History
Received: 15 December 2022
Accepted after revision: 06 March 2023
Accepted Manuscript online:
06 March 2023
Article published online:
12 April 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Onajole OK, Govender K, Govender P, Van Helden PD, Kruger HG, Maguire GE. M, Muthusamy K, Pillay M, Wiid I, Govender T. Eur. J. Med. Chem. 2009; 44: 4297
- 1b Rey-Carrizo M, Barniol-Xicota M, Ma C, Frigolé-Vivas M, Torres E, Naesens L, Llabrés S, Juárez-Jiménez J, Luque FJ, DeGrado WF, Lamb RA, Pinto LH, Vázquez S. J. Med. Chem. 2014; 57: 5738
- 2a Michalson ET, Szmuszkovics J. Prog. Drug Res. 1989; 33: 135
- 2b Joubert J, Geldenhuys WJ, Van der Schyf CJ, Oliver DW, Kruger HG, Govender T, Malan SF. ChemMedChem 2012; 7: 375
- 2c Gante J. Angew. Chem. Int. Ed. 1994; 33: 1699
- 2d Govender T, Kruger HG, Makatini M, Onajole OK. Struct. Chem. 2008; 19: 719
- 3a Bartsch RA, Eley M, Marchand AP, Shukla R, Kumar KA. Tetrahedron 1996; 52: 8979
- 3b Williams SM, Brodbelt JS, Marchand AP, Cal D, Mlinarie-Majerski K. Anal. Chem. 2002; 74: 4423
- 3c Kotha S, Cheekatla SR. J. Org. Chem. 2018; 83: 6315
- 3d Marchand AP, Chong HS, Ganguly B. Tetrahedron: Asymmetry 1999; 10: 4695
- 4a Hattori Y, Miyajima T, Sakai M, Nagase Y, Nemoto N. Polymer 2008; 49: 2825
- 4b Khardin AP, Radchenko SS. Russ. Chem. Rev. 1982; 51: 272
- 5a Kaszynski P, Friedli AC, Michl J. J. Am. Chem. Soc. 1992; 114: 601
- 5b Kotha S. Tetrahedron 1994; 50: 3639
- 6a Olah G. Cage Hydrocarbons 1990
- 6b Osawa E, Yonemitsu O. Carbocyclic Caged Compounds . VCH; New York: 1992
- 7a Mehta G, Srikrishna A, Rao SK, Reddy KR, Acharya KA, Puranik VG, Tavale SS, Guru Row TN. J. Org. Chem. 1987; 52: 457
- 7b Rao CN, Khan FA. Org. Biomol. Chem. 2015; 13: 2768
- 7c Mehta G, Singh VK, Rao KS. Tetrahedron Lett. 1980; 21: 1369
- 7d Marchand AP, Sorokin VD, Rajagopal D, Bott SG. Heterocycles 1995; 40: 223
- 7e Kotha S, Cheekatla SR. ChemistrySelect 2019; 4: 13440
- 8 Eaton PE, Cole TW. J. Am. Chem. Soc. 1964; 86: 962
- 9 Delarue Bizzini L, Müntener T, Häussinger D, Neuburger M, Mayor M. Chem. Commun. 2017; 53: 11399
- 10 Levandovsky IA, Sharapa DI, Cherenkova OA, Gaidai AV, Shubina TE. Russ. Chem. Rev. 2010; 79: 10051026
- 11a Kotha S, Cheekatla S, Mhatre D. Synthesis 2017; 49: 5339
- 11b Swager TM, Romero NA. Synfacts 2018; 14: 0247
- 11c Kotha S, Ansari S, Cheekatla SR, Dipak MK. Tetrahedron 2020; 76: 130856
- 11d Kotha S, Cheekatla SR, Chaurasia UN. Tetrahedron 2020; 76: 13169
- 12a Eaton PE, Alberici F, Cassar L, Monti F, Neri C, Nodari N. US Patent US4943302A, 1990
- 12b Eaton PE, Nodari N, Neri C, Cassar L, Monti F, Alberici F. European Patent EP0364051B1, 1990
- 13a Mehta G, Srikrishna A. Chem. Rev. 1997; 97: 671
- 13b Mehta G, Kotha S. J. Org. Chem. 1985; 50: 5537
- 13c Lannoye G, Kotha S, Wehrli S, Cook JM. J. Org. Chem. 1988; 53: 2327
- 14 Li Y, Zhang L, Wang W, Liu Y, Sun D, Li H, Chen L. Bioorg. Chem. 2022; 128: 106106
- 15a Geldenhuys WJ, Malan SF, Bloomquist JR, Marchand AP, Vander Schyt CJ. Med. Res. Rev. 2005; 25: 21
- 15b Marchand AP, Kumar KA, Mckim AS, Mlinarie-Majerski K, Kragol G. Tetrahedron 1997; 53: 3467
- 16a Morrill C, Funk TW, Grubbs RH. Tetrahedron Lett. 2004; 45: 7733
- 16b Choi TL, Chatterjee AK, Grubbs RH. Angew. Chem. Int. Ed. 2001; 40: 1277
- 16c Chatterjee AK, Sanders DP, Grubbs RH. Org. Lett. 2002; 4: 1939
- 17 Cookson RC, Crundwell E, Hill RR, Hudec J. J. Chem. Soc. 1964; 3062
- 18 Chatterjee AK, Choi TL, Sanders DP, Grubbs RH. J. Am. Chem. Soc. 2003; 125: 11360
- 19 Geldenhuys WJ, Malan SF, Murugesan T. Bioorg. Med. Chem. 2004; 12: 1799
- 20a Marchand AP, Kumar KA, McKim AS, Mlinarié-Majerski K, Kragol G. Tetrahedron 1997; 53: 3467
- 20b Govender T, Hariprakasha HK, Kruger HG, Marchand AP. Tetrahedron: Asymmetry 2003; 14: 1553
- 21a Kotha S, Sreenivasachary N, Mohanraja K, Durani S. Bioorg. Med. Chem. Lett. 2001; 11: 1421
- 21b Kotha S, Chavan AS, Shaikh M. J. Org. Chem. 2012; 77: 482
- 21c Kotha S, Khedkar P. J. Org. Chem. 2009; 74: 5667
- 21d Kotha S, Chavan SA. J. Org. Chem. 2010; 75: 4319
- 21e Kotha S, Meshram M, Khedkar P, Banerjee S, Deodhar D. Beilstein J. Org. Chem. 2015; 11: 1833
- 22 Kotha S, Krishna GK, Halder S, Misra S. Org. Biomol. Chem. 2011; 9: 5597