Nef-isocyanide-Perkow access to novel pyrazolone derivations containing a cyclic ketene dithioacetal moiety

References

• Hack, D.; Dürr, A. B.; Deckers, K.; Chauhan, P.; Seling, N.; Rübenach, L.; Mertens, L.; Raabe, G.; Schoenebeck, F.; Enders, D. Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver-Catalysis. Angew. Chem. Int. Ed. Engl. 2016, 55, 1797-1800. DOI: 10.1002/anie.201510602.
   PubMed Web of Science ®Google Scholar
• Li, J.-H.; Du, D.-M. Organocatalyzed Cascade Aza-Michael/Michael Addition for the Asymmetric Construction of Highly Functionalized Spiropyrazolone Tetrahydroquinolines. Chem. Asian J. 2014, 9, 3278-3286. DOI: 10.1002/asia.201402706.
   PubMed Web of Science ®Google Scholar
• Zea, A.; Alba, A.-N. R.; Mazzanti, A.; Moyano, A.; Rios, R. Highly Enantioselective Cascade Synthesis of Spiropyrazolones. Org. Biomol. Chem. 2011, 9, 6519-6523. DOI: 10.1039/c1ob05753g.
   PubMed Web of Science ®Google Scholar
• Chauhan, P.; Mahajan, S.; Enders, D. Asymmetric Synthesis of Pyrazoles and Pyrazolones Employing the Reactivity of Pyrazolin-5-One Derivatives. Chem. Commun. 2015, 51, 12890-12907. DOI: 10.1039/C5CC04930J.
   PubMed Web of Science ®Google Scholar
• Jiang, X.; Liu, L.; Zhang, P.; Zhong, Y.; Wang, R. Catalytic Asymmetric β,γ Activation of α,β‐Unsaturated γ‐Butyrolactams: Direct Approach to β,γ‐Functionalized Dihydropyranopyrrolidin‐2‐Ones. Angew. Chem. Int. Ed. 2013, 52, 11329-11333. DOI: 10.1002/anie.201302622.
   PubMedGoogle Scholar
• Bao, X.; Wang, B.; Cui, L.; Zhu, G.; He, Y.; Qu, J.; Song, Y. An Organocatalytic Asymmetric Friedel-Crafts Addition/Fluorination Sequence: Construction of Oxindole-Pyrazolone Conjugates Bearing Vicinal Tetrasubstituted Stereocenters. Org. Lett. 2015, 17, 5168-5171. DOI: 10.1021/acs.orglett.5b02470.
   PubMed Web of Science ®Google Scholar
• Yang, S.; Shen, L.-L.; Kim, Y.-J.; Jeong, J.-H. Effective and Novel Enantioselective Preparation of Pyranopyrazoles and Pyranocoumarins That Is Catalyzed by a Quinine-derived Primary Amine. Org. Biomol. Chem. 2016, 14, 623-630. DOI: 10.1039/C5OB01656H.
   PubMed Web of Science ®Google Scholar
• Yetra, S. R.; Mondal, S.; Mukherjee, S.; Gonnade, R. G.; Biju, A. T. Enantioselective Synthesis of Spirocyclohexadienones by NHC‐Catalyzed Formal [3 + 3] Annulation Reaction of Enals. Angew. Chem. Int. Ed. 2016, 55, 268. 272. DOI: org/10.1002/ange.201507802
   PubMed Web of Science ®Google Scholar
• Yavari, I.; Sheykhahmadi, J.; Saffarian, H.; Zahedi, N.; Bahemmat, S.; Halvagar, M. R. A Convenient Synthesis of Functionalized Pyrazolones Bearing a Highly Twisted 1,3-butadiene Moiety with Skew Geometry. Synth. Commun. 2018, 48, 2608-2614. DOI: 10.1080/00397911.2018.1516292
   Web of Science ®Google Scholar
• Yavari, I.; Nematpour, M.; Sodagar, E. Formation of Spiro[indene-2,30 -pyrazole] derivatives from Hydrazonyl Chlorides and Ninhydrin-Malononitrile Adduct. Monatsh. Chem. 2015, 146, 2135-2138. DOI: 10.1007/s00706-015-1495-7.
   Web of Science ®Google Scholar
• Yavari, I.; Nematpour, M. Tandem Synthesis of Highly Functionalized N-Phosphorylated Sulfonamido-pyrazolone Derivatives. Tetrahedron Lett. 2013, 54, 5061-5063. DOI: 10.1016/j.tetlet.2013.07.035.
   Web of Science ®Google Scholar
• Yavari, I.; Seyfi, S.; Skoulika, S. A Convenient Synthesis of Functionalized Indenopyrazolones from Indan1,2,3-trione, Benzaldehydes, and Phenylhydrazine. Hca. 2012, 95, 1581-1585. DOI: 10.1002/hlca.201200053.
   Web of Science ®Google Scholar
• Chou, W. C.; Fang, J. M. Use of Ketene Dithioacetal as a Latent Carboxylic Acid in the Macrolactonization Applicable to the Synthesis of Dilactonic Pyrrolizidine Alkaloids. J. Org. Chem. 1996, 61, 1473-1477. DOI: 10.1021/jo951363y.
   Web of Science ®Google Scholar
• Tominaga, Y.; Matsuda, Y. Synthesis of Heterocyclic Compounds Using Nitro Dithioacetal. J. Het. Chem. 1985, 22, 937-949. DOI: 10.1002/jhet.5570220401.
   Web of Science ®Google Scholar
• Potts, K. T.; Cipullo, M. J.; Ralli, P.; Theodoridis, G. Ketene Dithioacetals as Synthetic Intermediates. A Versatile Synthesis of Pyridines, Polypyridinyls, and Pyrylium Salts. J. Am. Chem. Soc. 1981, 103, 3585-3586. DOI: 10.1021/ja00402a062.
   Web of Science ®Google Scholar
• Pan, L.; Bi, X.; Liu, Q. Recent Developments of Ketene Dithioacetal Chemistry. Chem. Soc. Rev. 2013, 42, 125-1286. DOI: 10.1039/C2CS35329F
   Web of Science ®Google Scholar
• Chavan, S. M.; Toche, R. B.; Patil, V. M.; Aware, P. B.; Patil, P. S. Reactions of Ketene Dithioacetal for a New Versatile Synthesis of 4,5-Substituted 3-Aminothiophene-2-Carboxylate Derivatives. J. Sulfur. Chem. 2016, 37, 426-437. DOI: 10.1080/17415993.2016.1156117.
   Web of Science ®Google Scholar
• Yavari, I.; Saffarian, H.; Naeimabadi, M. A One-pot Synthesis of Novel Cyclic Ketene Dithioacetals from Nef-isocyanide-Perkow Adduct. J. Sulfur. Chem. 2017, 38, 679-685. DOI: 10.1080/17415993.2017.1347173.
   Web of Science ®Google Scholar
• Spisa, F. L.; Tron, G. C.; El-Kaïm, L. The Nef Reaction of Isocyanides. Synthesis 2014, 46, 829-841. DOI: 10.1055/s-0033-1338596.
   Web of Science ®Google Scholar
• Coffinier, D.; El-Kaim, L.; Grimaud, L. Isocyanide-Based Two-Step Three-Component Keteneimine Formation. Org. Lett. 2009, 11, 1825-1827. DOI: 10.1021/ol9004432.
   PubMed Web of Science ®Google Scholar
• Yavari, I.; Pashazadeh, R.; Hosseinpour, R.; Ghanbari, E.; Skoulika, S. Nef-isocyanide-Perkow Synthesis of New Polarized Olefins Containing 2-Dicyanomethylene-2,3-Dihydrothiazole and 2-Dicyanomethylene-1,3-Dithiole Moieties. Tetrahedron 2013, 69, 2462-2467. DOI: 10.1016/j.tet.2013.01.023.
   Web of Science ®Google Scholar
• Farrugia, L. J.; Win, G. X. Software for Guided Crystal Structure Analysis. J. Appl. Crystallogr. 1999, 32, 837-838. DOI: 10.1107/S0021889899006020.
   Web of Science ®Google Scholar
• Allen, F. H.; Johnson, O.; Shields, G. P.; Smith, B. R.; Towler, M. CIF Applications. XV. enCIFer: A Program for Viewing, Editing and Visualizing CIFs. J. Appl. Crystallogr. 2004, 37, 335-338. DOI: 10.1107/S0021889804003528.
   Web of Science ®Google Scholar
• Burnett, M. N.; Johnson, C. K. ORTEP-III Report ORNL-6895. Oak Ridge National Laboratory: Oak Ridge, TN; 1996.
   Google Scholar