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Synthesis
DOI: 10.1055/a-2499-2559
DOI: 10.1055/a-2499-2559
feature
Nickel-Catalyzed Regioselective Access to Dibenzo[c,f][1,2]thiazepine 5,5-Dioxides and Dibenzo[b,e]azepines
T.G. gratefully acknowledges funding from the Science and Engineering Research Board (SERB), India for a TARE fellowship (TAR/2023/000045). S.S.A. is grateful to the Council of Scientific and Industrial Research (CSIR), India for a Junior Research Fellowship (JRF).
Abstract
An effective technique that yields dibenzo[c,f][1,2]thiazepine 5,5-dioxide and dibenzo[b,e]azepine derivatives through nickel-catalyzed regioselective intramolecular acetylene hydroarylation is reported. The developed method proceeds without the need for any additional external ligand. This protocol tolerates different functional groups and furnishes the desired products regioselectively in good to excellent yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2499-2559.
- Supporting Information
Publication History
Received: 09 October 2024
Accepted after revision: 09 December 2024
Accepted Manuscript online:
09 December 2024
Article published online:
17 January 2025
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References
- 1a Drews J. Science 2000; 287: 1960
- 1b Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Curr. Med. Chem. 2003; 10: 925
- 1c Stappers F, Broeckx R, Leurs S, Bergh LV. D, Agten J, Lambrechts A, Heuvel DV. D, Smaele DD. Org. Process Res. Dev. 2002; 6: 911
- 2a Silvestri R, Marfè G, Artico M, La Regina G, Lavecchia A, Novellino E, Morgante M, Di Stefano C, Catalano G, Filomeni G, Abruzzese E, Ciriolo MR, Russo MA, Amadori S, Cirilli R, La Torre F, Salimei PS. J. Med. Chem. 2006; 49: 5840
- 2b Lebegue N, Gallet S, Flouquet N, Carato P, Pfeiffer B, Renard P, Leonce S, Pierre A, Chavatte P, Berthelot P. J. Med. Chem. 2005; 48: 7363
- 3a Zia-ur-Rehman M, Choudary JA, Ahmad S, Siddiqui HL. Chem. Pharm. Bull. 2006; 54: 1175
- 3b Valente C, Guedes RC, Moreira R, Iley J, Gut J, Rosenthal PJ. Bioorg. Med. Chem. Lett. 2006; 16: 4115
- 3c Francotte P, De Tullio P, Goffin E, Dintilhac G, Graindorge E, Fraikin P, Lestage P, Danober L, Thomas J.-Y, Caignard D.-H, Pirotte B. J. Med. Chem. 2007; 50: 3153
- 3d Supuran CT. Nat. Rev. Drug Discovery 2008; 7: 168
- 3e Ganguly AK, Alluri SS, Caroccia D, Biswas D, Wang C.-H, Kang E, Zhang Y, McPhail AT, Carroll SS, Burlein C, Munshi V, Orth P, Strickland C. J. Med. Chem. 2011; 54: 7176
- 3f Gilleron P, Wlodarczyk N, Houssin R, Farce A, Laconde G, Goossens J.-F, Lemoine L, Pommery N, Henichart JP, Millet R. Bioorg. Med. Chem. Lett. 2007; 17: 5465
- 4a The Alkaloids, Vol. 26. Simanek V, Brossi A. Academic Press; New York: 1985: 185
- 4b Lee S, Hwang S, Yu S, Jang W, Lee YM, Kim S. Arch. Pharm. Res. 2011; 34: 1065
- 4c Fang SD, Wang LK, Hecht SM. J. Org. Chem. 1993; 58: 5025
- 4d Hegan DC, Lu Y, Stachelek GC, Crosby ME, Bindra RS, Glazer PM. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 2201
- 5a Wong GT, Manfra D, Poulet FM, Zhang Q, Josien H, Bara T, Engstrom L, Pinzon-Ortiz M, Fine JS, Lee H.-J, Zhang L, Higgins GA, Parker EM. J. Biol. Chem. 2004; 279: 12876
- 5b Keller L, Beaumont S, Liu J.-M, Thoret S, Bignon JS, Wdzieczak-Bakala J, Dauban P, Dodd RH. J. Med. Chem. 2008; 51: 3414
- 5c Nair JS, Sheikh T, Ho AL, Schwartz GK. Anticancer Res. 2013; 33: 1307
- 5d Laconde G, Depreux P, Berthelot P, Pommery N, Hénichart J.-P. Eur. J. Med. Chem. 2005; 40: 167
- 6a Bravo RD, Canepa AA. Synth. Commun. 2002; 32: 3675
- 6b Orazi OO, Corral RA, Bravo R. J. Heterocycl. Chem. 1986; 23: 1701
- 7a Lee J, Zhong Y.-L, Reamer RA, Askin D. Org. Lett. 2003; 5: 4175
- 7b Mondal S, Debnath S. Synthesis 2014; 46: 368
- 8 Chiacchio U, Corsaro A, Rescifina A, Bkaithan M, Grassi G, Piperno A, Privitera T, Romeo TG. Tetrahedron 2001; 57: 3425
- 9a Metz P, Seng D, Fröhlich R. Synlett 1996; 741
- 9b Rogachev VO, Metz P. ARKIVOC 2007; (v): 167
- 9c Rogatchov VO, Bernsmann H, Schwab P, Fröhlich R, Wibbeling B, Metz P. Tetrahedron Lett. 2002; 43: 4753
- 9d Plietker B, Seng D, Fröhlich R, Metz P. Tetrahedron 2000; 56: 873
- 9e Rogachev VO, Filimonov VD, Fröhlich R, Kataeva O, Metz P. Heterocycles 2006; 67: 589
- 9f Greig IR, Tozer MJ, Wright PT. Org. Lett. 2001; 3: 369
- 10 Rolfe A, Young K, Volp K, Schoenen F, Neuenswander B, Lushington GH, Hanson PR. Org. Lett. 2001; 3: 369
- 11a Vasudevan A, Tseng PS, Djuric SW. Tetrahedron Lett. 2006; 47: 8591
- 11b Merten S, Fröhlich R, Kataeva O, Metz P. Adv. Synth. Catal. 2005; 347: 754
- 11c Paquette LA, Barton WR. S, Gallucci JC. Org. Lett. 2004; 6: 1313
- 11d Paquette LA, Dura RD, Fosnaugh N, Marshall S. J. Org. Chem. 2006; 71: 8438
- 11e Liu X.-Y, Li C.-H, Che C.-M. Org. Lett. 2006; 8: 2707
- 12a Dauban P, Dodd RH. Org. Lett. 2000; 2: 2327
- 12b Sherman ES, Chemler SR, Tan TB, Gerlits O. Org. Lett. 2004; 6: 1573
- 12c Dauban P, Sanière L, Tarrade A, Dodd RH. J. Am. Chem. Soc. 2001; 123: 7707
- 12d Zeng W, Chemler SR. J. Am. Chem. Soc. 2007; 129: 12948
- 13a Liang J.-L, Yuan S.-X, Chan PW. H, Che C.-M. Org. Lett. 2002; 4: 4507
- 13b Padwa A, Flick AC, Leverett CA, Stengel T. J. Org. Chem. 2004; 69: 6377
- 14 Wrobel Z. Tetrahedron Lett. 2000; 41: 7365
- 15 Bressy C, Menant C, Piva O. Synlett 2005; 577
- 16 Jeon KO, Rayabarapu D, Rolfe A, Volp K, Omar I, Hanson PR. Tetrahedron 2009; 65: 4992
- 17 Wanner J, Harned AM, Probst DA, Poon KW. C, Klein TA, Snelgrove KA, Hanson PA. Tetrahedron Lett. 2002; 43: 917
- 18 Ho KF, Fung DC. W, Wong WY, Chan WH, Lee AW. M. Tetrahedron Lett. 2001; 42: 3121
- 19 Long DD, Dahl R, Jolivet C, Marshall WJ, Termin AP. Tetrahedron Lett. 2002; 43: 4407
- 20 Harling JD, Steel PG, Woods TM, Yufit DS. Org. Biomol. Chem. 2007; 5: 3472
- 21 van Boxtel LJ, Keorbe S, Noltemeyer M, de Meijere A. Eur. J. Org. Chem. 2001; 12: 2283
- 22 Wang H, Luo Y, Hou X, Wu J. Dalton Trans. 2013; 4410
- 23 Majumdar KC, Mondal S, De N. Synthesis 2009; 3127
- 24 Majumdar KC, Mondal S. Chem. Rev. 2011; 111: 7749
- 25a Joardar S, Bhattacharyya A, Das S. Synthesis 2014; 46: 3121
- 25b Joardar S, Chakravorty S, Das S. Synlett 2015; 26: 359
- 26a Ghosh T. New J. Chem. 2017; 41: 2927
- 26b Ghosh T. Synth. Commun. 2018; 48: 1338
- 26c Ghosh T. ChemistrySelect 2019; 4: 4747
- 26d Bhakta S, Ghosh T. Adv. Synth. Catal. 2020; 362: 5257
- 26e Bhakta S, Ghosh T. ChemCatChem 2021; 13: 828
- 26f Ghosh T. Asymmetric Nickel-Catalyzed Reactions . In Comprehensive Chirality, 2nd ed. Cossy J. Elsevier; Amsterdam: 2024: 234-353
- 27 Ananikov PO. ACS Catal. 2015; 5: 1964
- 28 Zhang WS, Ji DW, Li Y. Nat. Commun. 2023; 14: 651
- 29 Mondal S, Debnath S, Das B. Tetrahedron 2015; 71: 476