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Synthesis 2016; 48(23): 4199-4206
DOI: 10.1055/s-0035-1562474
DOI: 10.1055/s-0035-1562474
paper
Facile Synthesis of Some Chlorinated and Heteroatom-Rich Monocyclic β-Lactams via the Staudinger Reaction of Acyclic S-Alkylisothioureas
Weitere Informationen
Publikationsverlauf
Received: 29. Mai 2016
Accepted after revision: 11. Juni 2016
Publikationsdatum:
15. August 2016 (online)
Abstract
The optimized preparation of a rare class of highly functionalized (chlorinated and heteroatom-rich) monocyclic β-lactams by the Staudinger reaction of reactive acyclic S-alkylisothioureas with dichloroketene is presented. The use of acyclic S-alkylisothioureas in the Staudinger β-lactam synthesis has been demonstrated for the first time. The present method is mild, economical and wide in scope.
Key words
monocyclic β-lactams - dichloroketene - acyclic S-alkylisothioureas - Staudinger reaction - chlorinated - heteroatom richSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562474.
- Supporting Information
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References
- 1 Dua R, Shrivastava S, Sonwane SK, Srivastava SK. Adv. Biol. Res. 2011; 5: 120
- 2a Arya N, Jagdale AY, Patil TA, Yeramwar SS, Holikatti SS, Dwivedi J, Shishoo CJ, Jain KS. Eur. J. Med. Chem. 2014; 74: 619
- 2b Masouda MS, Alib AE, Nasrc NM. J. Chem. Pharm. Res. 2014; 6: 28
- 2c von Nussbaum F, Brands M, Hinzen B, Weigand S, Häbich D. Angew. Chem. Int. Ed. 2006; 45: 5072
- 2d Singh GS. Mini-Rev. Med. Chem. 2004; 4: 69
- 2e Singh GS. Mini-Rev. Med. Chem. 2004; 4: 93
- 3a Papp-Wallace KM, Mallo S, Bethel CR, Taracila MA, Hujer AM, Fernández A, Gatta JA, Smith KM, Xu Y, Page MG. P, Desarbre E, Bou G, Bonomo RA. J. Antimicrob. Chemother. 2014; 69: 682
- 3b Pierrat OA, Strisovsky P, Christova Y, Large J, Ansell K, Bouloc N, Smiljanic E, Freeman M. ACS Chem. Biol. 2011; 6: 325
- 3c Fischer JR, Meroueh SO, Mobashery S. Chem. Rev. 2005; 105: 395
- 4 Veinberg G, Vorona M, Shestakova I, Kanepe I, Lukevics E. Curr. Med. Chem. 2003; 10: 1741
- 5 Shaikh S, Fatima J, Shakil S, Rizvi SM. D, Kamal MA. Saudi J. Biol. Sci. 2015; 22: 90
- 6a Dražić T, Vazdar K, Vazdar M, Ðaković M, Mikecin A.-M, Kralj M, Malnar M, Hećimović S, Habuš I. Tetrahedron 2015; 71: 9202
- 6b Dekeukeleire S, D’hooghe M, Vanwalleghem M, Van Brabandt W, De Kimpe N. Tetrahedron 2012; 68: 10827
- 6c Núñez-Villanueva D, Bonache MA, Infantes L, García-López MT, Martín-Martínez M, González-Muñiz R. J. Org. Chem. 2011; 76: 6592
- 6d Palomo C, Oiarbide M. Top. Heterocycl. Chem. 2010; 22: 211
- 6e Dekeukeleire S, D’hooghe M, Törnroos KW, De Kimpe N. J. Org. Chem. 2010; 75: 5934
- 6f Alcaide B, Almendros P, Aragoncillo C. Chem. Rev. 2007; 107: 4437
- 6g Van Brabandt W, Dejaegher Y, Van Landeghem R, De Kimpe N. Org. Lett. 2006; 8: 1101
- 6h Van Brabandt W, Vanwalleghem M, D’hooghe M, De Kimpe N. J. Org. Chem. 2006; 71: 7083
- 6i Alcaide B, Almendros P. Curr. Med. Chem. 2004; 11: 1921
- 6j Deshmukh AR. A. S, Bhawal BM, Krishnaswamy D, Govande VV, Shinkre BA, Jayanthi A. Curr. Med. Chem. 2004; 11: 1889
- 6k Veinberg G, Vorona M, Shestakova I, Kanepe I, Lukevics E. Curr. Med. Chem. 2003; 10: 1741
- 6l Ojima I. Acc. Chem. Res. 1995; 28: 383
- 7a Vergely I, Boggetto N, Okochi V, Golpayegani S, Reboud-Ravaux M, Kobaiter R, Joyeau R, Wakselman M. Eur. J. Med. Chem. 1995; 30: 199
- 7b Khalafallah AK, Selim MA, El-Hamed RM. A, Elmaghraby MA, Soleiman HA, Raslan MA. Ind. J. Chem., Sect B: Org. Chem. Incl. Med. Chem. 1995; 34: 1066
- 7c Joyeau R, Molines H, Labia R, Wakselman M. J. Med. Chem. 1988; 31: 370
- 8a Konaklieva MI. Antibiotics 2014; 3: 128
- 8b Orbegozo T, Burel F, Jubault P, Pannecoucke X. Tetrahedron 2013; 69: 4015
- 8c Nisha, Mehra V, Hopper M, Patel N, Hall D, Wrischnik LA, Land KM, Kumar V. Med. Chem. Commun. 2013; 4: 1018
- 8d Dodiya AM, Shihory NR, Desai NC. Synth. Commun. 2012; 42: 3230
- 8e Kostova MB, Myers CJ, Beck TN, Plotkin BJ, Green JM, Boshoff HI. M, Barry CE, Deschamps JR, Konaklieva MI. Bioorg. Med. Chem. 2011; 19: 6842
- 8f Zarei M, Mohamadzadeh M. Tetrahedron 2011; 67: 5832
- 8g Ruf S, Neudert G, Gurtler S, Grunert R, Bednarski PJ, Otto H. Monatsh. Chem. 2008; 139: 847
- 8h Rohini RM, Kumar DR. H, Kumar RR, Ghate M. J. Pharm. Res. 2008; 7: 239
- 8i Powers JC, Asgian JL, Ekici OD, James KE. Chem. Rev. 2002; 102: 4639
- 8j Clemente A, Domingos A, Grancho AP, Iley J, Moreira R, Neres J, Palma N, Santana AB, Valente E. Bioorg. Med. Chem. Lett. 2001; 11: 1065
- 8k McKittrick BA, Ma K, Huie K, Yumibe N, Davis H, Clader JW, Czarniecki M. J. Med. Chem. 1998; 41: 752
- 8l Yoshida C, Hori T, Momonoi K, Nagumo K, Nakano J, Kitani T, Fukuoka Y, Saikawa I. J. Antibiot. 1985; 38: 1536
- 8m George J, Gholam H. US Patent 4385175, 1983
- 8n Shafie E, Siddieg F. Asian J. Chem. 1991; 3: 225
- 9 Abdulla RF, Fuhr KH. J. Med. Chem. 1975; 18: 625
- 10 Doz V, Opitz G, Koch J. Angew. Chem. 1963; 75: 167
- 11 Bose AK, Kugajevsky I. Tetrahedron 1967; 23: 957
- 12a Bizzo HR, Antunes OA. C, Gemal AL. Heterocycl. Commun. 2003; 9: 359
- 12b Sharma SD, Kaur V, Bhutani P, Khurana JP. S. Bull. Chem. Soc. Jpn. 1992; 65: 2246
- 12c Sharma SD, Arora SK, Mehra U. Ind. J. Chem. 1985; 24B: 895
- 12d Bose AK, Kapur JC, Manhas MS. Synthesis 1974; 891
- 13 Staudinger H, Meyer J. Helv. Chim. Acta 1919; 2: 635
- 14 Sahoo SK, Khatun N, Jena HS, Patel BK. Inorg. Chem. 2012; 51: 10800
- 15 Marwaha A, Singh P, Mahajan MP. Tetrahedron 2006; 62: 5474