Straightforward synthesis of novel spiroether derivatives

References

• (a) Hirasawa, Y.; Morita, H.; Shiro, M.; Kobayashi, J. Sieboldine A, a Novel Tetracyclic Alkaloid from Lycopodium Sieboldii, Inhibiting Acetylcholinesterase. Org. Lett. 2003, 5, 3991–3993. DOI: 10.1021/ol035560s. ;
   PubMed Web of Science ®Google Scholar
  (b)Aoki, S.; Watanabe, Y.; Sanagawa, M.; Setiawan, A.; Kotoku, N.; Kobayashi, M, M. Cortistatins A, B, C, and D, Anti-Angiogenic Steroidal Alkaloids, from the Marine Sponge Corticium Simplex. J. Am. Chem. Soc. 2006, 128, 3148–3149. DOI: 10.1021/ja057404h.
   PubMed Web of Science ®Google Scholar
  (c) Katsoulis, I. A.; Kythreoti, G.; Papakyriakou, A.; Koltsida, K.; Anastasopoulou, P.; Stathakis, C. I.; Mavridis, I.; Cottin, T.; Saridakis, E.; Vourloumis, D. Synthesis of 5,6-Spiroethers and Evaluation of Their Affinities for the Bacterial a Site. Chembiochem 2011, 12, 1188–1192. DOI: 10.1002/cbic.201100076.
   PubMed Web of Science ®Google Scholar
• (a) Bloch, P.; Tamm, C. Isolation and Structure of Pseurotin A, a Microbial Metabolite OfPseudeurotium Ovalis STOLK with an Unusual Heterospirocyclic System. Helv. Chim. Acta 1981, 64, 304–315. DOI: 10.1002/hlca.19810640131.
   Web of Science ®Google Scholar
  (b) Barreca, M. L.; Rao, A.; De Luca, L.; Zappalà, M.; Gurnari, C.; Monforte, P.; De Clercq, E.; Van Maele, B.; Debyser, Z.; Witvrouw, M.; et al. Efficient 3D Database Screening for Novel HIV-1 in Inhibitors. J. Chem. Inf. Comput. Sci. 2004, 44, 1450–1455. DOI: 10.1021/ci034296e.
   PubMedGoogle Scholar
  (c) Krämer, H.-J.; Kessler, D.; Hipler, U.-C.; Irlinger, B.; Hort, W.; Bödeker, R.-H.; Steglich, W.; Mayser, P. Pityriarubins, Novel Highly Selective Inhibitors of Respiratory Burst from Cultures of the Yeast Malassezia Furfur: Comparison with the Bisindolylmaleimide Arcyriarubin A. Chembiochem 2005, 6, 2290–2297. DOI: 10.1002/cbic.200500163.
   PubMed Web of Science ®Google Scholar
  (d) Ishikawa, M.; Ninomiya, T. Chemical Modification of Pseurotin A: One-Pot Synthesis of Synerazol and Pseurotin E and Determination of Absolute Stereochemistry of Pseurotin E. J. Antibiot. 2008, 61, 692–695. DOI: 10.1038/ja.2008.99.
   PubMed Web of Science ®Google Scholar
  (e) Peddibhotla, S. 3-Substituted-3-Hydroxy-2-Oxindole, an Emerging New Scaffold for Drug Discovery with Potential anti-Cancer and Other Biological Activities. Curr. Bioact. Compound. 2009, 5, 20–38. DOI: 10.2174/157340709787580900.
   Google Scholar
  (f) Barbier, V.; Couty, F.; David, O. R. P. Furan-2,3-Diones as Masked Dipoles: Synthesis of Isotetronic Acids and Mechanistic Considerations. Tetrahedron 2016, 72, 5646–5651. DOI: 10.1016/j.tet.2016.07.072.
   Web of Science ®Google Scholar
• (a) Nakajima, M.; Itoi, K.; Takamatsu, Y.; Kinoshita, T.; Okazaki, T.; Kawakubo, K.; Shindo, M.; Honma, T.; Tohjigamori, M.; Haneishi, T. Hydantocidin: A New Compound with Herbicidal Activity from Streptomyces Hygroscopicus. J Antibiot (Tokyo) 1991, 44, 293–300. DOI: 10.7164/antibiotics.44.293.
   PubMed Web of Science ®Google Scholar
  (b) Renard, A.; Lhomme, J.; Kotera, M. Synthesis and Properties of Spiro Nucleosides Containing the Barbituric Acid Moiety. J. Org. Chem. 2002, 67, 1302–1307. DOI: 10.1021/jo016194y.
   PubMed Web of Science ®Google Scholar
• (a) Lafont, O. Influence de La Lipophilie Sur L’oxydation Biologique D’une Chaîne Méthyl-3 Butyle En Série Barbiturique. Eur. J. Med. Chem. 1988, 23, 427–432. DOI: 10.1016/0223-5234(88)90139-0.
   Web of Science ®Google Scholar
  (b) Barreca, M. L.; Rao, A.; De Luca, L.; Zappalà, M.; Gurnari, C.; Monforte, P.; De Clercq, E.; Van Maele, B.; Debyser, Z.; Witvrouw, M.; et al. Efficient 3D Database Screening for Novel HIV-1 in Inhibitors. J. Chem. Inf. Comput. Sci. 2004, 44, 1450–1455.
   PubMedGoogle Scholar
  (c) Barreca, M. L.; Luca, L.; De; Ferro, S.; Rao, A.; Monforte, A.-M.; Chimirri, A. Computational and Synthetic Approaches for the Discovery of HIV-1 Integrase Inhibitors. Arkivoc 2006, 2006, 224–244. DOI: 10.3998/ark.5550190.0007.717.
   Web of Science ®Google Scholar
  (d) Zhou, Q.; Xiang, J.; Tang, Y.; Liao, J.; Yu, C.; Zhang, H.; Li, L.; Yang, Y.; Xu, G. Investigation on the Interaction between a Heterocyclic Aminal Derivative, SBDC, and Human Serum Albumin. Colloids Surf. B Biointerfaces 2008, 61, 75–80. DOI: 10.1016/j.colsurfb.2007.07.007.
   PubMed Web of Science ®Google Scholar
  (e) Zhou, Q.; Xiang, J.; Tang, Y.; Liao, J.; Yu, C.; Du, H.; Yang, Q.; Xu, G. Interaction of Spiro[(2R,3R,4S)-4-Benzyloxy-2,3-Iso-Propylidenedioxy-1-Oxacyclopentane-5,5′-(2-Nitromethylene-1,3-Diazacyclohexane)] with. Bovine Serum Albumin. Pestic. Biochem. Physiol. 2008, 92, 43–47. DOI: 10.1016/j.pestbp.2008.06.002.
   Web of Science ®Google Scholar
  (f) Haghdadi, M.; Price, L. S.; Bosra, H. G. Analysis of Anomeric Effects in Some Oxa Diaza Spiro Decan Derivatives by DFT Molecular Orbital Calculations. J. Mol. Struct. Theo. Chem. 2010, 947, 58–67. DOI: 10.1016/j.theochem.2010.01.041.
   Web of Science ®Google Scholar
• (a) Kappe, C. O. Biologically Active Dihydropyrimidones of the Biginelli-type-a literature survey. Eur. J. Med. Chem. 2000, 35, 1043–1052. DOI: 10.1016/S0223-5234(00)01189-2.
   PubMed Web of Science ®Google Scholar
  (b) Brands, M.; Endermann, R.; Gahlmann, R.; Krüger, J.; Raddatz, S. Dihydropyrimidinones-a new class of anti-staphylococcal antibiotics. Bioorg. Med. Chem. Lett. 2003, 13, 241–245. DOI: 10.1016/S0960-894X(02)00880-6.
   PubMed Web of Science ®Google Scholar
  (c) Vdovina, S. V.; Mamedov, V. A. New Potential of the Classical Biginelli Reaction. Russ. Chem. Rev. 2008, 77, 1017–1053. DOI: 10.1070/RC2008v077n12ABEH003894.
   Google Scholar
• Pallenberg, A. J.; White, J. D. The Synthesis and Absolute Configuration of (+)-Leptosphaerin. Tetrahedron. Lett. 1986, 27, 5591–5594. DOI: 10.1016/S0040-4039(00)85273-9.
   Web of Science ®Google Scholar
• Nishikawa, M.; Tsurumi, Y.; Namiki, T.; Yoshida, K.; Okuhara, M. Studies on WF-3681, a Novel Aldose Reductase Inhibitor. I. Taxonomy, Fermentation, Isolation and Characterization. J. Antibiot. (Tokyo) 1987, 40, 1394–1399. DOI: 10.7164/antibiotics.40.1394.
   PubMed Web of Science ®Google Scholar
• Pearce, A. N.; Appleton, D. R.; Babcock, R. C.; Copp, B. R.; Distomadines, A. and B, Novel 6-Hydroxyquinoline Alkaloids from the New Zealand Ascidian. Pseudodistoma Aureum. Tetrahedron. Lett. 2003, 44, 3897–3899. DOI: 10.1016/S0040-4039(03)00831-1.
   Web of Science ®Google Scholar
• (a) Toyoda-Ono, Y.; Maeda, M.; Nakao, M.; Yoshimura, M.; Sugiura-Tomimori, N.; Fukami, H. 2-O-(beta-D-Glucopyranosyl)ascorbic Acid, a Novel Ascorbic Acid Analogue Isolated from Lycium Fruit. J. Agric. Food Chem. 2004, 52, 2092–2096. DOI: 10.1021/jf035445w.
   PubMed Web of Science ®Google Scholar
  (b) Gein, V. L.; Yankin, A. N.; Nosova, N. V.; Dmitriev, M. V. Baeyer–Villiger Oxidation of N 1,N 3,2-Triaryl-6-Hydroxy-6-Methyl-4-Oxocyclohexane-1,3-Dicarboxamides. Russ. J. Org. Chem. 2016, 52, 379–382. DOI: 10.1134/S1070428016030143.
   Web of Science ®Google Scholar
• (a) Bohlmann, F.; Zdero, C.; King, R. M.; Robinson, H. Hirsutinolides and Other Sesquiterpene Lactones from Vernonia Species. Phytochemistry 1982, 21, 695–699. DOI: 10.1016/0031-9422(82)83168-3.
   Web of Science ®Google Scholar
  (b) Adamczeski, M.; Quiñoà, E.; Crews, P. Novel Sponge-Derived Amino Acids. 5.1Structures, Stereochemistry, and Synthesis of Several New Heterocycles. J. Am. Chem. Soc. 1989, 111, 647–654. DOI: 10.1021/ja00184a037.
   Web of Science ®Google Scholar
  (c) Keates, S. E.; Loewus, F. A.; Helms, G. L.; Zink, D. L. 5-O-(α-D-Galactopyranosyl)-D-Glycero-Pent-2-Enono-1,4-Lactone: Characterization in the Oxalate-Producing Fungus, Sclerotinia Sclerotiorum. Phytochemistry 1998, 49, 2397–2401. DOI: 10.1016/S0031-9422(98)00450-6.
   PubMed Web of Science ®Google Scholar
  (d) Enders, D.; Dyker, H.; Leusink, F. R. Enantioselective Synthesis of Protected Isotetronic Acids. Chem. Eur. J. 1998, 4, 311–320. DOI: 10.1002/(SICI)1521-3765(19980210)4:2 < 311::AID-CHEM311 > 3.3.CO;2-C.
   Web of Science ®Google Scholar
• Kato, S.; Dryhurst, G. Electrochemical Oxidation of Barbituric Acids in Aqueous Solution in the Absence of Chloride Ion. J. Electroanal. Chem. Interfacial Electrochem. 1977, 80, 181–199. DOI: 10.1016/S0022-0728(77)80113-7.
   Web of Science ®Google Scholar
• (a) Teimouri, M. B.; Abbasi, T.; Khavasi, H. R. Multicomponent Tandem Synthesis of Oxospirobicyclic Butenolidobarbiturates. J. Chem. Res. 2010, 34, 310–314. DOI: 10.3184/030823410X12746990145128.
   Web of Science ®Google Scholar
  (b) Teimouri, M. B.; Abbasi, T. Facile Synthesis of Oxaspirobicyclic Butenolides via a Domino Michael Addition/Aldol Reaction/γ-Lactonization Sequence. Tetrahedron 2010, 66, 3795–3800. DOI: 10.1016/j.tet.2010.03.058.
   Web of Science ®Google Scholar
• (a) Jalilzadeh, M.; Pesyan, N. N. New Strategy for the Synthesis of 5-Aryl-1H,1’H-Spiro[Furo[2,3-d]Pyrimidine-6,5’-Pyrimidine]2,2’,4,4’,6’(3H,3’H,5H)-Pentaones and Their Sulfur Analogues. Bull. Korean Chem. Soc. 2011, 32, 3382–3388. DOI: 10.5012/bkcs.2011.32.9.3382.
   Web of Science ®Google Scholar
  (b) Jalilzadeh, M.; Noroozi Pesyan, N.; Rezaee, F.; Rastgar, S.; Hosseini, Y.; Şahin, E. New One-Pot Synthesis of Spiro[Furo[2,3-d]Pyrimidine-6,5′-Pyrimidine]Pentaones and Their Sulfur Analogues. Mol. Divers. 2011, 15, 721–731. DOI: 10.1007/s11030-011-9302-9.
   PubMed Web of Science ®Google Scholar
  (c) Hosseini, Y.; Rastgar, S.; Heren, Z.; Büyükgüngörc, O.; Pesyan, N. N. One-Pot New Barbituric Acid Derivatives Derived from the Reaction of Barbituric Acids with BrCN and Ketones. J. Chin. Chem. Soc. 2011, 58, 309–318. DOI: 10.1002/jccs.201190031.
   Web of Science ®Google Scholar
  (d)Teimouri, M. B.; Akbari-Moghaddam, P.; Motaghinezhad, M. M. Urotropine–Bromine Promoted Synthesis of Functionalized Oxaspirotricyclic Furopyrimidines via a Domino Knoevenagel Condensation/Michael Addition/α-Bromination/Williamson Cycloetherification Sequence in Water. Tetrahedron 2013, 69, 6804–6809. DOI: 10.1016/j.tet.2013.06.030.
   Web of Science ®Google Scholar
  (e) Noroozi Pesyan, N.; Shokr, A.; Gharib, A.; Tunç, T.; Sahin, E. Regioselective One-Pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β-Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et 3 N. J. Chin. Chem. Soc. 2015, 62, 234–242. DOI: 10.1002/jccs.201400224.
   Web of Science ®Google Scholar
  (f) Teimouri, M. B.; Akbari-Moghaddam, P. Molecular Iodine-Catalysed Tandem Synthesis of Oxospirotricyclic Furopyrimidines in Water. J. Chem. Res. 2016, 40, 196–198. DOI: 10.3184/174751916X14568468874639.
   Google Scholar
• Elinson, M. N.; Merkulova, V. M.; Ilovaisky, A. I.; Nikishin, G. I. Cascade Assembling of Isatins and Barbituric Acids: Facile and Efficient Way to 2′′H -Dispiro[Indole-3,5′-Furo[2,3-d]Pyrimidine-6′,5′′-Pyrimidine]-2,2′,2′′,4′,4′′,6′′-(1H,1′H,1′′H,3′H,3′′H)-Hexone Scaffold. J. Heterocycl. Chem. 2013, 50, 1236–1241. DOI: 10.1002/jhet.1699..
   Web of Science ®Google Scholar
• Giarrusso, J.; Do, D. T.; Johnson, J. S. Chemoselective and Diastereoconvergent Cu(II)-Catalyzed Aerobic Endoperoxidation of Polycarbonyls. Org. Lett. 2017, 19, 3107–3110. DOI: 10.1021/acs.orglett.7b01225.. .
   PubMed Web of Science ®Google Scholar
• Hunter, A. C.; Schlitzer, S. C.; Stevens, J. C.; Almutwalli, B.; Sharma, I. A Convergent Approach to Diverse Spiroethers through Stereoselective Trapping of Rhodium Carbenoids with Gold-Activated Alkynols. J. Org. Chem. 2018, 83, 2744–2752. DOI: 10.1021/acs.joc.7b03196.
   PubMed Web of Science ®Google Scholar
• Jursic, B. S.; Stevens, E. D. Preparation of Nitrogen Heterocycles of Spiro[Furo[2,3‐ d] ‐Pyrimidine]. Pyrimidine Derivatives. Synth. Commun 2004, 34, 3915–3923. DOI: 10.1081/SCC-200034786.
   Web of Science ®Google Scholar
• (a) Renard, A.; Kotera, M.; Lhomme, J. Synthesis of Spirannic Nucleosides and Their Incorporation into Oligonucleotides. Nucleosid. Nucleotid. 1999, 18, 1437–1438. DOI: 10.1080/07328319908044746.
   Web of Science ®Google Scholar
  (b) Renard, A.; Lhomme, J.; Kotera, M. Synthesis and Properties of Spiro Nucleosides Containing the Barbituric Acid Moiety. J. Org. Chem. 2002, 67, 1302–1307. DOI: 10.1021/jo016194y.
   PubMed Web of Science ®Google Scholar
• Song, H. N.; Son, J. S.; Seong, M. R.; Kim, J. N. The Reaction of Ninhydrin with β-Acylpyruvates: Novel Spiro Compounds Formation. Synth. Commun. 1998, 28, 687–692. DOI: 10.1080/00397919808005941.
   Web of Science ®Google Scholar
• Tattersall, J.; Taylor, J. B. Novel Heterocyclic Spirobenzofurans. J. Chem. Soc. 970, 7, 931–933. DOI: 10.1039/j39700000931.
   Web of Science ®Google Scholar
• Xiong, Y.-J.; Shi, S.-Q.; Hao, W.-J.; Tu, S.-J.; Jiang, B. A New Dehydrogenative [4 + 1] Annulation between Para -Quinone Methides (p -QMs) and Iodonium Ylides for the Synthesis of 2,3-Dihydrobenzofurans. Org. Chem. Front. 2018, 5, 3483–3487. DOI: 10.1039/C8QO00950C.
   Web of Science ®Google Scholar
• (a) Gein, V. L.; Yankin, A. N.; Nosova, N. V.; Dmitriev, M. V.; Slepukhin, P. A. One-Pot Multicomponent Synthesis of Highly Substituted Bicyclo[2.2.2]Octane Derivatives Using Bismuth Nitrate as a Catalyst. Tetrahedron Lett. 2016, 57, 2441–2444. DOI: 10.1016/j.tetlet.2016.04.082.
   Web of Science ®Google Scholar
  (b) Gein, V. L.; Yankin, A. N.; Nosova, N. V.; Dmitriev, M. V.; Nasakin, O. E. Formation of 6-Aryl-2-Methyl-4-Oxo-N,N’-Diphenyl-2-Cyclohexene-1,3-Dicarboxamides from Acetoacetanilide and Aromatic Aldehydes Catalyzed by a Mixture of Aryl Amines and Iodine. Russ. J. Gen. Chem. 2016, 86, 58–61. DOI: 10.1134/S1070363216010114.
   Web of Science ®Google Scholar
  (c) Gein, V. L.; Nosova, N. V.; Yankin, A. N.; Bazhina, A. Y.; Dmitriev, M. V. An Eco-Friendly Stereoselective Synthesis of Novel Derivatives of Indeno[1,2- b] Pyrrole and Indeno[1,2- c] Pyridazine. Polycycl. Aromat. Compd. 2019, in press. DOI: 10.1080/10406638.2019.1602061. ;
   Web of Science ®Google Scholar
  (d) Yankin, A. N.; Nosova, N. V.; Dmitriev, M. V.; Gein, V. L. Synthesis of 1-Aryl-3a,8b-Dihydroxy-3-(1-Hydroxyethylidene)-1,3,3а,8b-Tetrahydroindeno[1,2-b]Pyrrole-2,4-Diones. Russ. J. Org. Chem. 2016, 52, 206–208. DOI: 10.1134/S107042801602007X.
   Web of Science ®Google Scholar
  (e) Gein, V. L.; Nosova, N. V.; Vagapova, A. V.; Dozmorova, N. V.; Yankin, A. N. Reactions of 2-Acetyl-5-Hydroxy-5-Methyl-3-Phenylcyclohexanone and Alkyl 4-Hydroxy-4-Methyl-2-Oxo-6-Phenylcyclohexanecarboxylates with Nucleophilic Reagents. Russ. J. Gen. Chem. 2019, 89, 1353–1359. DOI: 10.1134/S1070363219070016.
   Web of Science ®Google Scholar
  (f) Gein, V. L.; Nosova, N. V.; Yankin, A. N.; Bazhina, A. Y.; Dmitriev, M. V. Stereoselective Synthesis of Novel Functionalized Cyclohexanone Derivatives via the Condensation of Aromatic Aldehydes with Acetoacetamide and the Influence of the Ortho-Effect and Autocondensation. Tetrahedron. Lett. 2019, 60, 1592–1596. DOI: 10.1016/j.tetlet.2019.05.023.
   Web of Science ®Google Scholar
• (a) Gein, V. L.; Bobrovskaya, O. V.; Russkikh, A. A.; Dmitriev, M. V.; Yankin, A. N. Synthesis of Methyl 4-Aryl-4-Oxo-2-{4-[(1,3-Thiazol-2-Yl)-Sulfamoyl]Phenylamino}but-2-Enoates and Their Reactions with Ninhydrin. Russ. J. Org. Chem. 2019, 55, 602–607. DOI: 10.1134/S107042801905004X.
   Web of Science ®Google Scholar
  (b) Gein, V. L.; Bobrovskaya, O. V.; Dmitriev, M. V. Synthesis of Methyl 4-Aryl-4-Oxo-2-[(4-Sulfamoylphenyl)Amino]but-2-Enoates and Their Reaction with Ninhydrin. Russ. J. Org. Chem. 2017, 53, 898–903. DOI: 10.1134/S1070428017060148.
   Web of Science ®Google Scholar
• CCDC 2004796 (for 6b) CCDC 2004797 (for 6h) Contain the Supplementary Crystallographic Data for this Paper. The Data Can be Obtained Free of Charge from The Cambridge Crystallographic Data Centre. http://www.ccdc.cam.ac.uk.
   Google Scholar
• Mosmann, T. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays. J. Immunol. Methods. 1983, 65, 55–63. DOI: 10.1016/0022-1759(83)90303-4.
   PubMed Web of Science ®Google Scholar
• CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171.NET).
   Google Scholar
• Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: A Complete Structure Solution, Refinement and Analysis Program. J. Appl. Crystallogr. 2009, 42, 339–341. DOI: 10.1107/S0021889808042726.
   Web of Science ®Google Scholar
• Sheldrick, G. M. A Short History of SHELX. Acta Crystallogr. A 2008, 64, 112–122. DOI: 10.1107/S0108767307043930.
   PubMed Web of Science ®Google Scholar
• Palatinus, L.; Chapuis, G. SUPERFLIP – a Computer Program for the Solution of Crystal Structures by Charge Flipping in Arbitrary Dimensions. J. Appl. Crystallogr. 2007, 40, 786–790. DOI: 10.1107/S0021889807029238.
   Web of Science ®Google Scholar
• Sheldrick, G. M. SHELXT - integrated space-group and crystal-structure determination. Acta Crystallogr. A Found Adv. 2015, 71, 3–8. DOI: 10.1107/S2053273314026370.
   PubMed Web of Science ®Google Scholar