Asymmetric [4+2] annulation of N-sulfonyl ketimines: access to N-heterocycles bearing 1,3-nonadjacent stereocenters with a quaternary carbon center

Abstract

An organocatalytic [4+2] annulation of N-sulfonyl ketimines with aminochalcones has been developed to afford the benzenesulfonamide fused tetrahydroquinazoline compounds under mild conditions with excellent stereoselectivity (up to 99% ee). This method provides a concise and efficient approach for the construction of N-heterocyclic compounds bearing 1,3-nonadjacent stereocenters with a quaternary carbon center.

Keywords

Benzenesulfonamide / tetrahydroquinazoline / 1 / 3-nonadjacent stereocenters / aminochalcones / N-sulfonyl ketimines / [4+2] annulation

References

[1] Ramakrishnan V,Haug J.MRK003, a γ-secretase inhibitor exhibits promising in vitro pre-clinical activity in multiple myeloma and non-Hodgkin’s lymphoma.Leukemia2012;26:340-8 PMCID:PMC4384189

[2] Wrobel J,Woolson SA.Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents.J Med Chem1992;35:4613-27

[3] Takeuchi Y,Satoh A,Shibata N.N-fluoro-3-cyclohexyl-3-methyl-2,3- dihydrobenzo[1,2-d]isothiazole 1,1-dioxide: an efficient agent for electrophilic asymmetric fluorination of enolates.J Org Chem1999;64:5708-11

[4] Zheng PC,Su S.Oxidative N-heterocyclic carbene-catalyzed γ-carbon addition of enals to imines: mechanistic studies and access to antimicrobial compounds.Chemistry2015;21:9984-7

[5] Oppolzer W,Kelly MJ,Blagg J.Chiral toluene-2,α-sultam auxiliaries: asymmetric diels-alder reactions of N-enoyl derivatives.Tetrahedron Lett1990;31:5015-8

[6] Michael JP.Quinoline, quinazoline and acridone alkaloids.Nat Prod Rep2008;25:166-87

[7] Shang XF,Liu YQ.Biologically active quinoline and quinazoline alkaloids part I.Med Res Rev2018;38:775-828 PMCID:PMC6421866

[8] Corbett JW,Rodgers JD.Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors.J Med Chem2000;43:2019-30

[9] Blackman A,Picker K,Thirasasana N.Hinckdentine-a: a novel alkaloid from the marine bryozoan hincksinoflustra denticulata.Tetrahedron Lett1987;28:5561-2

[10] Marschall M,Urban A.In vitro evaluation of the activities of the novel anticytomegalovirus compound AIC246 (letermovir) against herpesviruses and other human pathogenic viruses.Antimicrob Agents Chemother2012;56:1135-7 PMCID:PMC3264222

[11] Xu D,Kucerovy A,Repic O.An efficient synthesis of enantiopure SDZ 267-489 via a resolution/racemization method.Tetrahedron Asymmetry1996;7:747-54

[12] Braekman JC,Pasteeis JM.Tetraponerine-8, an alkaloidal contact poison in a neoguinean pseudomyrmecine ant, tetraponera sp.Z Naturforsch C1987;42:627-30

[13] Kem WR,LeFrancois S,Marszalec W.Nicotinic receptor inhibition by Tetraponera ant alkaloids.Cell Mol Neurobiol2004;24:535-51

[14] Rouchaud A.Synthesis of new analogues of the Tetraponerines.Eur J Org Chem2009;2009:2666-74

[15] Sakai R,Shimamoto K.Novel betaines from a micronesian sponge Dysidea herbacea.J Org Chem2004;69:1180-5

[16] Zhu J,Husson HP.Asymmetric synthesis XVIII: preparation of Chiral 1,2-diamines via the CN(R,S) Method. Application to the synthesis of an analogue of tetraponerine.Tetrahedron Lett1989;30:5137-40

[17] Stragies R.Enantioselective synthesis of Tetraponerines by Pd- and Ru-catalyzed domino reactions.J Am Chem Soc2000;122:9584-91

[18] Davies SG,Houlsby ITT,Thomson JE.Asymmetric synthesis of the tetraponerine alkaloids.J Org Chem2017;82:6689-702

[19] Bosque I,Guijarro A,Yus M.Concise total synthesis and stereochemical analysis of tetraponerines T3 and T4.J Org Chem2012;77:10340-6

[20] Bosque I,Loza MI.Natural tetraponerines: a general synthesis and antiproliferative activity.J Org Chem2014;79:3982-91

[21] Pacheco JC, Lipp A, Nauth AM, Acke F, Dietz JP, Opatz T. A highly active system for the metal-free aerobic photocyanation of tertiary amines with visible light: application to the synthesis of tetraponerines and crispine A.Chemistry2016;22:5409-15

[22] He YP,Chen DF,Gong LZ.Cascade hydroamination/redox reaction for the synthesis of cyclic aminals catalyzed by a combined gold complex and Brønsted acid.Chemistry2013;19:5232-7

[23] Sim JT,Kim SG.Stereoselective synthesis of benzosulfamidate-fused tetrahydroquinazoline scaffold via organocatalytic [4+2] cycloaddition of 2-amino-β-nitrostyrenses of cyclic N-sulfimines.Tetrahedron Lett2016;57:5907-10

[24] Kim YS,Kim SG.Organocatalytic enantioselective synthesis of 1,3-oxazinanes and hexahydropyrimidines via [4+2]-annulation of cyclic N-sulfimines.Asian J Org Chem2023;12:e202300022

[25] Mun D,Kim SG.Palladium-catalyzed decarboxylative [4+2] cycloaddition of vinyl benzoxazinanones with cyclic N-sulfimines: stereoselective synthesis­ of benzosulfamidate-fused tetrahydroquinazolines.Synthesis2019;51:2359-70

[26] Rouh H,Xu T.Aggregation-induced synthesis (AIS): asymmetric synthesis via chiral aggregates.Research2022;2022:9865108 PMCID:PMC9394053

[27] Tang Y,Yuan Q.Aggregation-induced catalysis: asymmetric catalysis with chiral aggregates.Research2023;6:0163 PMCID:PMC10254464

[28] Rouh H,Zhang S.Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry.RSC Adv2021;11:39790-6 PMCID:PMC9044656