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Synthesis 2015; 47(08): 1190-1194
DOI: 10.1055/s-0034-1380109
DOI: 10.1055/s-0034-1380109
paper
Zolimidine Analogues: The Synthesis of Imidazo[1,2-α]pyridine-Based Sulfilimines and Sulfoximines
Weitere Informationen
Publikationsverlauf
Received: 12. Dezember 2014
Accepted after revision: 20. Dezember 2014
Publikationsdatum:
28. Januar 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201508/lookinside/thumbnails/ss-2014-z0762-op_10-1055_s-0034-1380109-1.jpg)
Abstract
Zolimidine is a methylsulfonyl-substituted drug with an imidazo[1,2-α]pyridine core used for the treatment of peptic ulcer. Herein, we report the synthesis of unprecedented N-acetylsulfilimine and -sulfoximine analogues under mild conditions. Deprotection of the N-acetylsulfoximine allows the preparation of the corresponding NH-sulfoximine.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380109.
- Supporting Information
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References
- 1a Couty F, Evano G In Comprehensive Heterocyclic Chemistry III . Vol. 11. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Oxford: 2008: 409-500
- 1b Liu J, Chen Q. Huaxue Jinzhan 2010; 22: 631
- 1c Zhou J, Liu J, Chen Q. Youji Huaxue 2009; 29: 1708
- 2a Bagdi AK, Santra S, Monir K, Hajra A. Chem. Commun. 2015; 51: 1555
- 2b Koubachi J, El Kazzouli S, Bousmina M, Guillaumet G. Eur. J. Org. Chem. 2014; 5119
- 3 For a selected application in the field of optoelectronics, see: Douhal A, Amat-Guerri F, Acuña AU. Angew. Chem., Int. Ed. Engl. 1997; 36: 1514
- 4 For a review on pharmacological applications, see: Enguehard-Gueiffier C, Gueiffier A. Mini-Rev. Med. Chem. 2007; 7: 888
- 5 For a selected example, see: Fisher MH, Lusi A. J. Med. Chem. 1972; 15: 982
- 6a Lhassani M, Chavignon O, Chezal JM, Teulade JC, Chapat JP, Snoeck R, Andrei G, Balzarini J, Clerc ED, Gueiffier A. Eur. J. Med. Chem. 1999; 34: 271
- 6b Hamdouchi C, de Blas J, del Prado M, Gruber J, Heinz BA, Vance L. J. Med. Chem. 1999; 42: 50
- 6c Kotovskaya SK, Baskakova ZM, Charushin VN, Chupakhin ON, Belanov EF, Bormotov NI, Balakhnin SM, Serova OA. Pharm. Chem. J. 2005; 39: 574
- 6d Bode ML, Gravestock D, Moleele SS, van der Westhuyzen CW, Pelly SC, Steenkamp PA, Hoppe CH, Khan T, Nkabinde LA. Bioorg. Med. Chem. 2011; 19: 4227
- 6e Enguehard-Gueiffier C, Musiu S, Henry N, Véron J.-B, Mavel S, Neyts J, Leyssen P, Paeshuyse J, Gueiffier A. Eur. J. Med. Chem. 2013; 64: 448
- 7a Shukla NM, Salunke DB, Yoo E, Mutz CA, Balakrishna R, David SA. Bioorg. Med. Chem. 2012; 20: 5850
- 7b Ramachandran S, Panda M, Mukherjee K, Choudhury N.-R, Tantry S.-J, Kedari CK, Ramachandran V, Sharma S, Ramya VK, Guptha S, Sambandamurthy V.-K. Bioorg. Med. Chem. Lett. 2013; 23: 4996
- 8a Baviskar AT, Madaan C, Preet R, Mohapatra P, Jain V, Agarwal A, Guchhait SK, Kundu CN, Banerjee UC, Bharatam PV. J. Med. Chem. 2011; 54: 5013
- 8b Dahan-Farkas N, Langley C, Rousseau AL, Yadav DB, Davids H, de Koning CB. Eur. J. Med. Chem. 2011; 46: 4573
- 9a Chermat R, Minaire Y, Chesneau MC, Simon P. Therapie 1977; 32: 643
- 9b Belohlavek D, Malfertheiner P. Scand. J. Gastroenterol. Suppl. 1979; 54: 44
- 9c Katsura Y, Nishino S, Takasugi H. Chem. Pharm. Bull. 1991; 39: 2937
- 9d Kaminsky JJ, Doweyko AM. J. Med. Chem. 1997; 40: 427
- 10a Georges GJ, Vercauteren DP, Evrard GH, Durant FV, George PG, Wick AE. Eur. J. Med. Chem. 1993; 28: 323
- 10b Langer SZ, Arbilla S, Benavides J, Scatton B. Adv. Biochem. Psychopharmacol. 1990; 46: 61
- 10c Boerner RJ, Möller HJ. Psychopharmakotherapie 1997; 4: 145
- 10d Hsu N, Jha SK, Coleman T, Frank MG. Behav. Brain Res. 2009; 201: 233
- 11 For a selected example, see: Mizushige K, Ueda T, Yukiiri K, Suzuki H. Cardiovasc. Drug Rev. 2002; 20: 163
- 12a Jenkinson S, Thomson M, McCoy D, Edelstein M, Danehower S, Lawrence W, Wheelan P, Spaltenstein A, Gudmundsson K. Antimicrob. Agents Chemother. 2010; 54: 817
- 12b Boggs S, Elitzin VI, Gudmundsson K, Martin MT, Sharp MJ. Org. Process Res. Dev. 2009; 13: 781
- 13a Rabenstein T, Fromm MF, Zolk O. Z. Gastroenterol. 2011; 49: 211
- 13b Scott LJ. Drugs 2014; 74: 2153
- 14 Almirante L, Polo L, Mugnaini A, Provinciali E, Rugarli P, Biancotti A, Gamba A, Murmann W. J. Med. Chem. 1965; 8: 305
- 15a Johnson CR. Acc. Chem. Res. 1973; 6: 341
- 15b Reggelin M, Zur C. Synthesis 2000; 1
- 15c Harmata M. Chemtracts 2003; 16: 660
- 15d Okamura H, Bolm C. Chem. Lett. 2004; 33: 482
- 15e Gais H.-J. Heteroat. Chem. 2007; 18: 472
- 15f Worch C, Mayer AC, Bolm C In Organosulfur Chemistry in Asymmetric Synthesis . Torru T, Bolm C. Wiley-VCH; Weinheim: 2008: 209
- 15g Bolm C. Latv. J. Chem. 2012; 49
- 15h Bizet V, Kowalczyk R, Bolm C. Chem. Soc. Rev. 2014; 43: 2426
- 16a Gnamm C, Jeanguenat A, Dutton AC, Grimm C, Kloer DP, Crossthwaite AJ. Bioorg. Med. Chem. Lett. 2012; 22: 3800
- 16b Sparks TC, Watson GB, Loso MR, Geng C, Babcock JM, Thomas JD. Pestic. Biochem. Phys. 2013; 107: 1
- 16c Bland DC, Ross RJr, Johnson PL, Johnson TC (Dow AgroSciences LLC) US Patent 20140005234 (A1), 2014
- 17a Foote KM, Wilhelmus J, Nissink M, Turner P (AstraZeneca) Patent WO2011154737 (A1), 2011
- 17b Lücking U. Angew. Chem. Int. Ed. 2013; 52: 9399 ; and references cited therein
- 17c Lücking U, Boehnke N, Scholz A, Lienau P, Siemeister G, Boemer U, Kosemund D, Bohlmann R (Bayer Pharma) Patent WO2014076111 (A1), 2014
- 18a Park SJ, Buschmann H, Bolm C. Bioorg. Med. Chem. Lett. 2011; 21: 4888
- 18b Chen XY, Park SJ, Buschmann H, De Rosa M, Bolm C. Bioorg. Med. Chem. Lett. 2012; 22: 4307
- 18c Lücking U, Jautelat R, Krüger M, Brumby T, Lienau P, Schäfer M, Briem H, Schulze J, Hillisch A, Reichel A, Wengner AM, Siemeister G. ChemMedChem 2013; 8: 1067
- 18d Park SJ, Baars H, Mersmann S, Buschmann H, Baron JM, Amann PM, Czaja K, Hollert H, Bluhm K, Redelstein R, Bolm C. ChemMedChem 2013; 8: 217
- 19 Goldberg FW, Kettle JG, Xiong J, Lin D. Tetrahedron 2014; 70: 6613
- 20a Zhou S, Gu Y, Liu M, Wu C, Zhao Y, Jia Z, Wang B, Xiong L, Yang N, Li Z. J. Agric. Food Chem. 2014; 62: 11054
- 20b Zhou S, Yan T, Li Y, Jia Z, Wang B, Zhao Y, Qiao Y, Xiong L, Li Y, Li Z. Org. Biomol. Chem. 2014; 12: 6643
- 21 For a single example on sulfoximine-based imidazo[1,2-α]quinolines, see: Ager IR, Barnes AC, Danswan GW, Hairsine PW, Kay DP, Kennewell PD, Matharu SS, Miller P, Robson P, Rowlands DA, Tully WR, Westwood R. J. Med. Chem. 1988; 31: 1098
- 22a Chandr Mohan D, Reddy Donthiri R, Nageswara Rao S, Adimurthy S. Adv. Synth. Catal. 2013; 355: 2217
- 22b Bagdi AK, Rahman M, Santra S, Majee A, Hajra A. Adv. Synth. Catal. 2013; 355: 1741
- 23 Garcí Mancheño O, Bistri O, Bolm C. Org. Lett. 2007; 9: 3809
- 24 For a similar reaction, see: Marhadour S, Bazin M.-A, Marchand P. Tetrahedron Lett. 2012; 53: 297
- 25 García Mancheño O, Bolm C. Org. Lett. 2007; 9: 2951
- 26 Okamura H, Bolm C. Org. Lett. 2004; 6: 1305
- 27a García Mancheño O, Dallimore J, Plant A, Bolm C. Org. Lett. 2009; 11: 2429
- 27b García Mancheño O, Dallimore J, Plant A, Bolm C. Adv. Synth. Catal. 2010; 352: 309
- 28a Bizet V, Buglioni L, Bolm C. Angew. Chem. Int. Ed. 2014; 53: 5639
- 28b Buglioni L, Bizet V, Bolm C. Adv. Synth. Catal. 2014; 356: 2209
- 29 Golchoubian H, Hosseinpoor F. Molecules 2007; 12: 304
- 30 Modified procedure based on deprotection conditions for trifluoroacetyl, see ref. 22.
For general information on imidazopyridines, see:
For reviews on the synthesis and functionalization of imidazo[1,2-α]pyridines, see:
For selected examples, see:
For selected examples, see:
For selected examples, see:
For selected examples, see:
For selected examples, see:
For selected examples, see:
For selected examples, see:
For overviews, see:
For sulfoximines used as insecticides, see:
For examples, see:
For examples, see:
For corresponding one-step gram-scale syntheses of zolimidine from 4′-methylsulfonylacetophenone, see:
For the procedure and an application in the synthesis of methionine and butionine sulfoximine, see: