Microwave-Assisted Synthesis of 2-Substituted 2-Thiazolines and 5,6-Dihydro-4H-1,3-thiazines

María C. Mollo; Juan A. Bisceglia; Natalia B. Kilimciler; Michele Mancinelli; Liliana R. Orelli

doi:10.1055/s-0039-1690822

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(11): 1666-1679
DOI: 10.1055/s-0039-1690822

paper

Microwave-Assisted Synthesis of 2-Substituted 2-Thiazolines and 5,6-Dihydro-4H-1,3-thiazines

María C. Mollo

^aUniversidad de Buenos Aires, CONICET, Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Junín 956, 1113 Buenos Aires, Argentina eMail: lorelli@ffyb.uba.ar

,

Juan A. Bisceglia

^aUniversidad de Buenos Aires, CONICET, Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Junín 956, 1113 Buenos Aires, Argentina eMail: lorelli@ffyb.uba.ar

,

Natalia B. Kilimciler

^aUniversidad de Buenos Aires, CONICET, Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Junín 956, 1113 Buenos Aires, Argentina eMail: lorelli@ffyb.uba.ar

,

Michele Mancinelli

^bDepartment of Industrial Chemistry ‘Toso Montanari’, University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy

,

Liliana R. Orelli ∗

^aUniversidad de Buenos Aires, CONICET, Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Junín 956, 1113 Buenos Aires, Argentina eMail: lorelli@ffyb.uba.ar

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Abstract

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Abstract

An efficient and general method for the synthesis of 2-substituted thiazolines and 5,6-dihydro-4H-1,3-thiazines is developed via microwave-assisted ring closure of ω-thioamidoalcohols promoted by ethyl polyphosphate (PPE). The cyclization reaction involves an S_N2-type mechanism and features the advantages of very short reaction times, high yields and a predictable stereochemical outcome. The acyclic precursors are prepared in high overall yields by an improved diacylation–thionation–saponification sequence from commercially available ω-aminoalcohols. The whole process is metal-free and operationally simple.

Key words

cyclic iminothioethers - thiazolines - dihydrothiazines - PPE - microwaves - thioamidoalcohols

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Referenzen

References
1 Schmidt E, Nelson J, Rasko D, Sudek S, Eisen J, Haygood M, Ravel J. Proc. Natl. Acad. Sci. U.S.A. 2005; 102: 7315
2 Boyce RJ, Mulqueen GC, Pattenden G. Tetrahedron Lett. 1994; 35: 5705
3 Carmeli S, Moore RE, Patterson GM. L. Tetrahedron Lett. 1991; 32: 2593
4 McKeever B, Pattenden G. Tetrahedron 2003; 59: 2713
5 Caujolle R, Baziard-Mouysset G, Favrot JD, Payard M, Loiseau PR, Amarouch H, Linas MD, Seguela JP, Loiseau PM, Bories C, Gayral P. Eur. J. Med. Chem. 1993; 28: 29
6 Bergeron RJ, Wiegand J, Dionis JB, Egli-Karmakka M, Frei J, Huxley-Tencer A, Peter HH. J. Med. Chem. 1991; 34: 2072
7 Tomizawa M, Cowan A, Casida JE. Toxicol. App. Pharm. 2001; 177: 77
8 McFarland JW, Howes HL. Jr, Conover LH, Lynch JE, Austin WC, Morgan DH. J. Med. Chem. 1970; 13: 113
9 McFarland JW, Ray VA. US 3629247A, 1971 ; Chem. Abstr. 1972, 76, 113235
10 Koch RC. US 3930001A, 1975 ; Chem. Abstr. 1976, 84, 175146
11 Ehrler J, Farooq S. Synlett 1994; 702
12 Zhou Z, Alper H. J. Org. Chem. 1996; 61: 1256
13 Jiao L, Zhang Q, Liang Y, Zhang S, Xu J. J. Org. Chem. 2006; 71: 815
14 Qi H, Yang Z, Xu J. Synthesis 2011; 723
15 Yamakuchi M, Matsunaga H, Tokuda R, Ishizuka T, Nakajima M, Kunieda T. Tetrahedron Lett. 2005; 46: 4019
16 McKeon SC, Müller-Bunz H, Guiry PJ. Eur. J. Org. Chem. 2009; 4833
17 Lu S, Du D, Zhang S, Xu J. Tetrahedron: Asymmetry 2004; 15: 3433
18 Nishio T, Kodama Y, Tsurumi Y. Phosphorus, Sulfur Silicon Relat. Elem. 2005; 180: 1449
19 Abrunhosa-Thomas I, Betz A, Denancé M, Dez I, Gaumont A, Gulea M. Heteroat. Chem. 2010; 21: 242
20 Vorbrüggen H, Krolikiewicz K. Tetrahedron Lett. 1981; 22: 4471
21 Wipf P, Wang X. J. Comb. Chem. 2002; 4: 656
22 Seijas JA, Vázquez-Tato MP, Crecente-Campo J. Tetrahedron 2008; 64: 9280
23 Hojati SF, Nezhadhoseiny SA. J. Serb. Chem. Soc. 2012; 77: 1181
24 Bazgir A, Amini MM, Fazaeli Y. Open Catal. J. 2009; 2: 163
25 Baltork IM, Moghadam M, Tangestaninejad S, Mirkhani V, Hojati SF. Catal. Commun. 2008; 9: 1153
26 Trose M, Lazreg F, Lesieur M, Cazin CS. J. Green Chem. 2015; 17: 3090
27 Busacca CA, Dong Y, Spinelli EM. Tetrahedron Lett. 1996; 37: 2935
28 Katritzky AR, Cai C, Suzuki K, Singh SK. J. Org. Chem. 2004; 69: 811
29 Charette AB, Chua P. J. Org. Chem. 1998; 63: 908
30 Pathak U, Bhattacharyya S, Dhruwansh V, Pandey LK, Tank R, Suryanarayana MV. S. Green Chem. 2011; 13: 1648
31 Fernández X, Fellous R, Duñach E. Tetrahedron Lett. 2000; 41: 3381
32 Petersson MJ, Jenkins DI, Loughlin WA. Org. Biomol. Chem. 2009; 7: 739
33 Wenker H. J. Am. Chem. Soc. 1935; 57: 1079
34 Nishio T, Konno Y, Ori M, Sakamoto M. Eur. J. Org. Chem. 2001; 3553
35 Kodama Y, Ori M, Nishio T. Helv. Chim. Acta 2005; 88: 187
36 Lafargue P, Guenot P, Lellouche JP. Synlett 1995; 171
37 Leflemme N, Marchand P, Gulea M, Masson S. Synthesis 2000; 1143
38 Pfund E, Lequeux T, Masson S, Vazeux M. Org. Lett. 2002; 4: 5
39 Mahler SG, Serra GL, Antonow D, Manta E. Tetrahedron Lett. 2001; 42: 8143
40 Abrunhosa I, Gulea M, Levillain J, Masson S. Tetrahedron: Asymmetry 2001; 12: 2851
41 Yan Z, Guan C, Yu Z, Tian W. Tetrahedron Lett. 2013; 54: 5788

42a Heredia DA, Larghi EL, Kaufman TS. Eur. J. Org. Chem. 2016; 1397
42b Stefańska B, Bontemps-Gracz MM, Antonini I, Martelli S, Arciemiuk M, Piwkowska A, Rogacka D, Borowski E. Bioorg. Med. Chem. 2005; 13: 1969
42c Yoshida Y, Mohri K, Isobe K, Itoh T, Yamamoto K. J. Org. Chem. 2009; 74: 6010
42d Sarma T, Panda PK, Anusha PT, Venugopal Rao S. Org. Lett. 2011; 13: 188
42e Aron ZD, Overman LE. Chem. Commun. 2004; 253
42f Geist JG, Lauw S, Illarionova V, Illarionov B, Fischer M, Gräwert T, Rohdich F, Eisenreich W, Kaiser J, Groll M, Scheurer C, Wittlin S, Alonso-Gómez JL, Bernd Schweizer W, Bacher A, Diederich F. ChemMedChem 2010; 5: 1092
42g Agbaje OC, Fadeyi OO, Adamson Fadeyi S, Myles LE, Okoro CO. Bioorg. Med. Chem. Lett. 2011; 21: 989
42h Hilmey DG, Paquette LA. Org. Lett. 2005; 7: 2067
42i Niemczak M, Czerniak K, Kopczyński T. New J. Chem. 2015; 39: 1868
42j López SE, Restrepo J, Salazar J. J. Chem. Res. 2007; 9: 497

43 Sharma A, Appukkuttan P, Van der Eycken E. Chem. Commun. 2012; 48: 1623

44a García MB, Torres RA, Orelli LR. Tetrahedron Lett. 2006; 47: 4857
44b Díaz JE, Bisceglia J. Á, Mollo MC, Orelli LR. Tetrahedron Lett. 2011; 52: 1895
44c Díaz JE, Gruber N, Orelli LR. Tetrahedron Lett. 2011; 52: 6443
44d Díaz JE, Vanthuyne N, Rispaud H, Roussel C, Vega D, Orelli LR. J. Org. Chem. 2015; 80: 1689
44e Díaz JE, Mollo MC, Orelli LR. Beilstein J. Org. Chem. 2016; 12: 2026
44f Mollo MC, Orelli LR. Org. Lett. 2016; 18: 6116
44g Díaz JE, Ranieri S, Gruber N, Orelli LR. Beilstein J. Org. Chem. 2017; 13: 1470
44h Díaz JE, Mazzanti A, Orelli LR, Mancinelli M. ACS Omega 2019; 4: 4712

45 Mollo MC, Kilimciler NB, Bisceglia JA, Orelli LR. Beilstein J. Org. Chem. 2019; 16: 32

46a Cherkasov RA, Kutyrev GA, Pudovick AN. Tetrahedron 1985; 41: 2567
46b Brillon D. Synth. Commun. 1992; 12: 297
46c Jesberger M, Davis TP, Barner L. Synthesis 2003; 1929
46d Ozturk T, Ertas E, Mert O. Chem. Rev. 2007; 107: 5210

47 Nishio T. J. Org. Chem. 1997; 62: 1106
48 Pathak U, Goud DR. Synthesis 2012; 44: 3678
49 Roggero J, Metzger J. Bull. Soc. Chim. Fr. 1963; 11: 2531 ; Chem. Abstr. 1964, 60, 4124

50a Batista JM. Jr, Blanch EW, da Silva Bolzani V. Nat. Prod. Rep. 2015; 32: 1280
50b He Y, Wang B, Dukor RK, Nafie LA. Appl. Spectrosc. 2011; 65: 699
50c Nafie LA. Nat. Prod. Commun. 2008; 3: 451

51 Morcuende A, Ors M, Valverde S, Herradon B. J. Org. Chem. 1996; 61: 5264
52 Xu Q, Li Z. Tetrahedron Lett. 2009; 50: 6838
53 Alcaide B, Casarrubios L, Domínguez G, Sierra MA. J. Org. Chem. 1993; 58: 3886
54 Phillips AP, Maggiolo A. J. Am. Chem. Soc. 1950; 72: 4920
55 Huneck S, Porzel A. Z. Naturforsch. B 2014; 49: 569
56 Loeppky RN, Shi J, Barnes CL, Geddam S. Chem. Res. Toxicol. 2008; 21: 295
57 Arm K, Tamura S, Masumizu T, Kawai K, Nakajima S, Akira U. Can. J. Chem. 1990; 68: 903
58 Rand AW, Montgomery J. ChemRxiv 2019;
59 Bu Q, Rogge T, Kotek V, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 765
60 Robbe Y, Fernandez JP, Chapat JP, Sentenac-Roumanou H, Fatome M. Eur. J. Med. Chem. 1985; 20: 16
61 Nguyen TB, Tran MQ, Ermolenko L, Al-Mourabit A. Org. Lett. 2014; 16: 310
62 Wipf P, Hayes GB. Tetrahedron 1998; 54: 6987
63 Kamila S, Biehl ER. J. Heterocycl. Chem. 2007; 44: 407
64 Hojati SF, Mohammadpoor-Baltork I, Maleki B, Gholizadeh M, Shafiezadeh F, Haghdoust M. Can. J. Chem. 2010; 88: 135
65 Yu Y, Chen H.-L, Wang L.-Y, Chen X.-Z, Fu B. Molecules 2009; 14: 4858
66 Babcock SH, Adams R. J. Am. Chem. Soc. 1937; 59: 2260

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