Heterogeneous Catalysis with Basic Compounds to Achieve the Synthesis and C–N Cleavage of Azetidin-2-ones under Microwave Irradiation

Adriana Galván; Fabiola N. de la Cruz; Francisco Cruz; Merced Martínez; Clarisa Villegas Gomez; Yolanda Alcaraz; José Manuel Domínguez; Francisco Delgado; Miguel A. Vázquez

doi:10.1055/s-0037-1611851

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(19): 3625-3637
DOI: 10.1055/s-0037-1611851

paper

Heterogeneous Catalysis with Basic Compounds to Achieve the Synthesis and C–N Cleavage of Azetidin-2-ones under Microwave Irradiation

Adriana Galván

^aDepartamento de Química, Universidad de Guanajuato, Noria Alta S/N, 36050, Guanajuato, Gto., México eMail: mvazquez@ugto.mx

,

Fabiola N. de la Cruz

^bDepartamento de Química Orgánica, Universidad Autónoma de Coahuila, Blvd. V. Carranza e Ing. José Cárdenas, 25280, Saltillo, Coahuila, México

,

Francisco Cruz

^aDepartamento de Química, Universidad de Guanajuato, Noria Alta S/N, 36050, Guanajuato, Gto., México eMail: mvazquez@ugto.mx

,

Merced Martínez

^aDepartamento de Química, Universidad de Guanajuato, Noria Alta S/N, 36050, Guanajuato, Gto., México eMail: mvazquez@ugto.mx

,

Clarisa Villegas Gomez

^aDepartamento de Química, Universidad de Guanajuato, Noria Alta S/N, 36050, Guanajuato, Gto., México eMail: mvazquez@ugto.mx

,

Yolanda Alcaraz

^cDepartamento de Farmacia, Universidad de Guanajuato, Noria Alta S/N, 36050, Guanajuato, Gto., México

,

José Manuel Domínguez

^dInstituto Mexicano del Petróleo, Eje Central Lázaro Cárdenas 152, 07730, Ciudad de México, México

,

Francisco Delgado

^eDepartamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas-IPN, Prolongación Carpio y Plan de Ayala S/N, 11340, Ciudad de México, México

,

Miguel A. Vázquez*

^aDepartamento de Química, Universidad de Guanajuato, Noria Alta S/N, 36050, Guanajuato, Gto., México eMail: mvazquez@ugto.mx

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Abstract

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Abstract

The synthesis of azetidin-2-ones with a completely heterogeneous catalysis is reported. The use of basic compounds as solid catalysts allowed for the synthesis of azetidin-2-ones under microwave irradiation without organic additives such as triethylamine. An excellent catalyst for this transformation was Mg-Al hydroxide (MAH). The present methodology offers the advantages of non-hazardous reaction conditions, short reaction times, high yields, and catalyst reusability. Different substitution groups were tested on the imines and acyl chlorides to explore the scope of the reaction. Unconventional N–C4 bond cleavage was detected in azetidin-2-ones. MAH was characterized by N₂ adsorption–desorption, X-ray diffraction (XRD), scanning electron microscopy (SEM), and high-resolution transmission electron microscopy (HR-TEM).

Key words

heterogeneous catalyst - Mg-Al hydroxide - azetidin-2-ones - ring opening - microwave irradiation

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Referenzen

References
1 Alcaide B, Almendros P. Chem. Rec. 2011; 11: 311
2 Pitts CR, Lectka T. Chem. Rev. 2014; 114: 7930
3 Arya N, Jagdale AY, Patil TA, Yeramwar SS, Holikatti SS, Dwivedi J, Shishoo CJ, Jain KS. Eur. J. Med. Chem. 2014; 74: 619
4 Clader JW. J. Med. Chem. 2004; 47: 1
5 Duane AB. Curr. Med. Chem. 2004; 11: 1873
6 Adlington RM, Baldwin JE, Chen B, Cooper SL, McCoull W, Pritchard GJ, Howe TJ, Becker GW, Hermann RB, McNulty AM, Neubauer BL. Bioorg. Med. Chem. Lett. 1997; 7: 1689
7 Annunziata R, Benaglia M, Cinquini M, Cozzi F, Puglisi A. Bioorg. Med. Chem. 2002; 10: 1813
8 Banik BK, Banik I, Becker FF. Eur. J. Med. Chem. 2010; 45: 846
9 Miller TM, Cleveland DW. Science 2005; 307: 361
10 O’Boyle NM, Carr M, Greene LM, Keely NO, Knox AJ. S, McCabe T, Lloyd DG, Zisterer DM, Meegan MJ. Eur. J. Med. Chem. 2011; 46: 4595
11 Borthwick AD, Weingarten G, Haley TM, Tomaszewski M, Wang W, Hu Z, Bedard J, Jin H, Yuen L, Mansour TS. Bioorg. Med. Chem. Lett. 1998; 8: 365
12 Biondi S, Long S, Panunzio M, Qin WL. Curr. Med. Chem. 2011; 18: 4223
13 Drawz SM, Bonomo RA. Clin. Microbiol. Rev. 2010; 23: 160
14 France S, Weatherwax A, Taggi AE, Lectka T. Acc. Chem. Res. 2004; 37: 592
15 Pérez-Llarena FJ, Bou G. Curr. Med. Chem. 2009; 16: 3740
16 Brandi A, Cicchi S, Cordero FM. Chem. Rev. 2008; 108: 3988
17 Jing-Fang W, Kuo-Chen C. Curr. Top. Med. Chem. 2013; 13: 1242
18 Shahid M, Sobia F, Singh A, Malik A, Khan HM, Jonas D, Hawkey PM. Crit. Rev. Microbiol. 2009; 35: 81
19 Sheldon RA, van Rantwijk F, van Langen LM, Wegman MA, Cao L, Janssen MH. A. In Synthesis of β-Lactam Antibiotics: Chemistry, Biocatalysis & Process Integration . Bruggink A. Springer Netherlands; Dordrecht: 2001
20 Tahlan K, Jensen SE. J. Antibiot. 2013; 66: 401
21 Worthington RJ, Melander C. J. Org. Chem. 2013; 78: 4207
22 Troisi CG. L, Pindinelli E. In Heterocyclic Scaffolds I: β-Lactams . Springer; Berlin: 2010
23 Furman B, Kałuza Z, Stencel A, Grzeszczyk B, Chmielewski M. In Heterocycles from Carbohydrate Precursors, Vol. 7 . El Ashry ES. H. Springer; Berlin: 2007: 101-132
24 Benaglia M, Cinquini M, Cozzi F. Eur. J. Org. Chem. 2000; 563
25 Stecko S, Furman B, Chmielewski M. Tetrahedron 2014; 70: 7817
26 Debecker DP, Gaigneaux EM, Busca G. Chem. Eur. J. 2009; 15: 3920
27 Karinen R, Vilonen K, Niemelä M. ChemSusChem 2011; 4: 1002
28 Navajas A, Campo I, Moral A, Echave J, Sanz O, Montes M, Odriozola JA, Arzamendi G, Gandía LM. Fuel 2018; 211: 173
29 Puértolas B, Imtiaz Q, Müller CR, Pérez-Ramírez J. ChemCatChem 2016; 9: 1579
30 Yan K, Wu G, Jin W. Energy Technol. 2016; 4: 354
31 Ishihara A, Ishida R, Ogiyama T, Nasu H, Hashimoto T. Fuel Process. Technol. 2017; 161: 17
32 Kshirsagar SW, Patil NR, Samant SD. Synth. Commun. 2011; 41: 1320
33 Li Q.-M, Zhang M, Wang C.-M, Zhu Y.-A, Zhou X.-G, Xie Z.-K. Mol. Catal. 2018; 446: 106
34 Appaturi JN, Selvaraj M, Abdul Hamid SB. Microporous Mesoporous Mater. 2018; 260: 260
35 Morales-Serna JA, Jaime-Vasconcelos MA, García-Ríos E, Cruz A, Angeles-Beltrán D, Lomas-Romero L, Negrón-Silva GE, Cárdenas J. RSC Adv. 2013; 3: 23046
36 Ramani A, Chanda BM, Velu S, Sivasanker S. Green Chem. 1999; 1: 163
37 Choudhary VR, Dumbre DK, Narkhede VS, Jana SK. Catal. Lett. 2003; 86: 229
38 Zeng H.-Y, Wang Y.-J, Feng Z, You K.-Y, Zhao C, Sun J.-W, Liu P.-l. Catal. Lett. 2010; 137: 94
39 Ionescu R, Pavel OD, Bırjegaa R, Zavoianu R, Angelescu E. Catal. Lett. 2010; 134: 309
40 Tantirungrotechai J, Chotmongkolsap P, Pohmakotr M. Microporous Mesoporous Mater. 2010; 128: 41
41 Thomas AB, Paradkar O, Nanda RK, Tupe PN, Sharma PA, Badhe R, Kothapalli L, Banerjee A, Hamane S, Deshpande A. Green Chem. Lett. Rev. 2010; 3: 293
42 Avasthi K, Yadav R, Khan T. J. Applicable Chem. 2014; 3: 1899
43 Avasthi RY. K, Bohre A. Eur. Chem. Bull. 2015; 4: 268
44 Babasaheb MG. L, Kendre V, Bhusare SR. Open J. Med. Chem. 2012; 2: 98
45 Li Z, Zhu A, Yang J. J. Heterocycl. Chem. 2012; 49: 1458
46 Cossio FP, Arrieta A, Sierra MA. Acc. Chem. Res. 2008; 41: 925
47 Banik BK, Barakat KJ, Wagle DR, Manhas MS, Bose AK. J. Org. Chem. 1999; 64: 5746
48 Pérez-Ruiz R, Sáez JA, Jiménez MC, Miranda MA. Org. Biomol. Chem. 2014; 12: 8428
49 Alcaide B, Almendros P, Redondo MC. Org. Lett. 2004; 6: 1765
50 Ramos R, Medellin-Castillo N, Jacobo-Azuara A, Mendoza J, Landin-Rodriguez LE, Martínez-Rosales J, Aragon-Piña A. J. Environ. Eng. Manage. 2008; 18: 301
51 Kim JW, He J, Yamaguchi K, Mizuno N. Chem. Lett. 2009; 38: 920
52 Vázquez MA, Landa M, Reyes L, Miranda R, Tamariz J, Delgado F. Synth. Commun. 2004; 34: 2705
53 Bennett JS, Charles KL, Miner MR, Heuberger CF, Spina EJ, Bartels MF, Foreman T. Green Chem. 2009; 11: 166
54 Pandey V, Chawla V, Saraf SK. Med. Chem. Res. 2012; 21: 844
55 Miyamura H, Morita M, Inasaki T, Kobayashi S. Bull. Chem. Soc. Jpn. 2011; 84: 588

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