Synthesis of Six-Membered Cyclic Sulfonimidamides

Abstract

A general synthetic route to six-membered cyclic N-aryl- and N-alkyl-substituted sulfonimidamides via an intramolecular ring closure of suitably functionalised acyclic sulfonimidamides is described. The structure of this new ring system was confirmed by various analytical methods and in one example by X-ray structural analysis.

Key words

sulfonimidamide - heterocycles - cyclisation - sulfur - intramolecular

• References

• 1a Levchenko ES, Sheinkman IE, Kirsanov AV. Zh. Obshch. Khim. 1960; 30: 1941 ; Chem. Abstr. 1961, 55, 6426
• 1b Levchenko ES, Derkach NY, Kirsanov AV. Zh. Obshch. Khim. 1962; 32: 1208 ; Chem. Abstr. 1963, 58, 1388
• 2a Johnson CR, Wambsgans A. J. Org. Chem. 1979; 44: 2278
• 2b Johnson CR, Jonsson EU, Wambsgans A. J. Org. Chem. 1979; 44: 2061
• 2c Johnson CR, Jonsson EU, Bacon CC. J. Org. Chem. 1979; 44: 2055
• 2d Okuma K, Koike T, Ohta H. J. Org. Chem. 1988; 53: 4190
• 2e Okuma K, Higuchi N, Kaji S, Takeuchi H, Ohta H, Matsuyama H, Kamigata N, Kobyashi M. Bull. Chem. Soc. Jpn. 1990; 63: 3223
• 2f Tsushima S, Yamada Y, Onami T, Oshima K, Chaney MO, Jones ND, Swartzendruber JK. Bull. Chem. Soc. Jpn. 1989; 62: 1167
• 2g Worch C, Atodiresei I, Raabe G, Bolm C. Chem. Eur. J. 2010; 16: 677
• 2h Mancheño OG, Bolm C. Beilstein J. Org. Chem. 2007; 3: No. 25
• 2i Pennington RL, Shab X, King SB. Bioorg. Med. Chem. Lett. 2005; 15: 2331
• 2j Sehgelmeble F, Janson J, Ray C, Rosqvist S, Gustavsson S, Nilsson LI, Minidis A, Holenz J, Rotticci D, Lundkvist J, Arvidsson PI. Chem. Med. Chem. 2012; 7: 396
• 2k Levchenko ES, Markovskii LN, Shermolovich YG. Russ. J. Org. Chem. 2000; 36: 143
• 3a Johnson CR, Lavergne OM. J. Org. Chem. 1993; 58: 1922
• 3b Azzaro S, Fensterbank L, Lacôte E, Malacria M. Synlett 2008; 2253
• 3c Azzaro S, Murr MD. E, Fensterbank L, Lacôte E, Malacria M. Synlett 2011; 849
• 3d Maldonado MF, Sehgelmeble F, Bjarnemark F, Svensson M, Åhman J, Arvidsson PI. Tetrahedron 2012; 68: 7456
• 3e Worch C, Bolm C. Synthesis 2008; 739
• 3f Borhade SR, Sandstorm A, Arvidsson PI. Org. Lett. 2013; 15: 1056
• 4a Leca D, Toussaint A, Mareau C, Fensterbank L, Lacôte E, Malacria M. Org. Lett. 2004; 6: 3573
• 4b Rashatasakhon P, Harmata M. Chemtracts: Org. Chem. 2006; 19: 143
• 5a Di Chenna PH, Robert-Peillard F, Dauban P, Dodd RH. Org. Lett. 2004; 6: 4503
• 5b Robert-Peillard F, Di Pablo C, Liang HC, Lescot C, Collet F, Dodd RH, Dauban P. Tetrahedron: Asymmetry 2010; 21: 1447
• 5c Liang C, Robert-Peillard F, Fruit C, Mueller P, Dodd RH, Dauban P. Angew. Chem. Int. Ed. 2006; 45: 4641
• 5d Lescot C, Darses B, Collet F, Retailleau P, Dauban P. J. Org. Chem. 2012; 77: 7232
• 6 Worch C, Bolm C. Synlett 2009; 2425
• 7a Steurer M, Bolm C. J. Org. Chem. 2010; 75: 3301
• 7b Lescot C, Darses B, Collet F, Retailleau P, Dauban P. J. Org. Chem. 2012; 77: 7232
• 7c Patureau FW, Worch C, Siegler MA, Spek AL, Bolm C, Reek JN. H. Adv. Synth. Catal. 2012; 354: 59
• 8a Kleemann HW, Brendel J, Schwark JR, Weichert A, Lang HJ, Albus U, Scholz W Hoechst AG, Frankfurt am Main, Germany: Patent EP 0771788 A2, 1997 ; Chem. Abstr. 1997, 127, 17500
• 8b Kleemann HW, Lang HJ, Schwark JR, Weichert A, Scholz W, Albus U Hoechst AG, Frankfurt am Main, Germany: Patent US 6057322 A, 2000 ; Chem. Abstr. 2000, 132, 293573
• 9a Paulini R, Breuninger D, von Deyn W, Bastiaans HM. M, Beyer C, Anspaugh DD, Oloumi-Sadeghi H BASF SE, Ludwigshafen, Germany: PCT Int. Appl WO2009156336 A1, 2009 ; Chem. Abstr. 2009, 152, 97451
• 9b Paulini R, von Deyn W, Bastiaans HM. M, Beyer C BASF SE, Ludwigshafen, Germany: PCT Int. Appl WO2011069955 A1, 2011 ; Chem. Abstr. 2011, 155, 93714
• 9c Gnamm C, Jeanguenat A, Dutton AC, Grimm C, Kloer DP, Crossthwaite AJ. Bioorg. Med. Chem. Lett. 2012; 22: 3800
• 10 Cathers BE, Schloss JV. Bioorg. Med. Chem. Lett. 1999; 9: 1527
• 11 Pemberton N, Garden H, Evertsson E, Bratt E, Lepisto M, Johannesson P, Svensson PH. ACS Med. Chem. Lett. 2012; 3: 574
• 12 Kresze G, Maschke A, Albrecht R, Bederke K, Patzschke HP, Smalla H, Trede A. Angew. Chem., Int. Ed. Engl. 1962; 1: 89
• 13 Gilman G, Morris HL. J. Am. Chem. Soc. 1926; 48: 2399
• 14a Harmata M, Zheng P, Huang PC, Gomes MG, Ying W, Ranyanil KO, Balan G, Calkins NL. J. Org. Chem. 2007; 72: 683
• 14b Wagner HU, Judelbaum A. Angew. Chem., Int. Ed. Engl. 1978; 17: 460
• 15 Other chlorinating agents like N-chlorobenzotriazole also gave similar results, but the separation of product 3 from benzotriazole was tedious.
• 16a Treatment of sulfonimidamide 3h or 3m with NaOEt in EtOH under reflux conditions led only to hydrolysis of ester functionality to give 4h or 4m (see ref. 11).
• 16b Using t-BuOK in refluxing toluene resulted in only 3 being recovered.
• 16c Under acidic conditions using PTSA in refluxing toluene, 3 was again recovered, with minor cleavage of the R¹NH-moiety being also observed.
• 17a Corey EJ, Durst T. J. Am. Chem. Soc. 1968; 90: 5548
• 17b Bowlus SB, Katzenellenbogen JA. Synth. Commun. 1974; 4: 137
• 17c Ruano JL. G, Parra A, Yuste F, Mastranzo VM. Synthesis 2008; 311
• 17d Uchino M, Sekiya M. Chem. Pharm. Bull. 1980; 28: 126
• 17e Mintz MJ, Walling C. Org. Synth. Coll. Vol. 5 . Wiley; New York: 1973: 184
• 18 The assignments of the aromatic H’s in substituents R¹ for compounds 5 has been made in analogy to the HMBC experiment of 5j (see Supporting Information).