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Pure Appl. Chem., 1999, Vol. 71, No. 6, pp. 979-988

http://dx.doi.org/10.1351/pac199971060979

Enaminones: versatile intermediates for natural product synthesis

J. P. Michael, C. B. de Koning, D. Gravestock, G. D. Hosken, A. S. Howard, C. M. Jungmann, R. W. M. Krause, A. S. Parsons, S. C. Pelly and T. V. Stanbury

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  • Ranade Adwait R., Georg Gunda I.: Enantioselective Synthesis of 3,4-Dihydro-1,2-oxazepin-5(2H)-ones and 2,3-Dihydropyridin-4(1H)-ones from β-Substituted β-Hydroxyaminoaldehydes. J. Org. Chem. 2014, 79, 984. <http://dx.doi.org/10.1021/jo402445r>
  • Suryavanshi Padmakar A., Sridharan Vellaisamy, Menéndez J. Carlos: A β-Enaminone-Initiated Multicomponent Domino Reaction for the Synthesis of Indoloquinolizines and Benzoquinolizines from Acyclic Precursors. Chem. Eur. J. 2013, 19, 13207. <http://dx.doi.org/10.1002/chem.201204594>
  • Cheikh Nawel, Villemin Didier, Bar Nathalie, Lohier Jean-François, Choukchou-Braham Nourredine, Mostefa-Kara Bachir, Sopkova Jana: A serendipitous conversion of enaminolactone nitriles with primary amines: a new synthesis of substituted 2-aminopyridine derivatives. Tetrahedron 2013, 69, 1234. <http://dx.doi.org/10.1016/j.tet.2012.10.108>
  • Ponpandian Thanasekaran, Muthusubramanian Shanmugam: Sequential deprotection–cyclisation reaction: stereoselective synthesis of azabicyclic β-enamino ester derivatives and (−) indolizidine 209D. Tetrahedron 2013, 69, 527. <http://dx.doi.org/10.1016/j.tet.2012.11.029>
  • Villemin Didier, Belhadj Zahira, Cheikh Nawel, Choukchou-Braham Noureddine, Bar Nathalie, Lohier Jean-François: Solventless convenient synthesis of new cyano-2-aminopyridine derivatives from enaminonitriles. Tetrahedron Letters 2013, 54, 1664. <http://dx.doi.org/10.1016/j.tetlet.2013.01.021>
  • Cunha Silvio, Filho Raimundo Francisco dos Santos, Saraiva Katharine Hodel, Azevedo-Santos Alene Vanessa, Menezes Diego: Synthesis of multi-functionalized 1-azabicycles through MAOS acid catalyzed formal aza-[3+3] cycloaddition of heterocyclic enaminones with oxazolones. Tetrahedron Letters 2013, 54, 3366. <http://dx.doi.org/10.1016/j.tetlet.2013.04.055>
  • Tolmacheva I. A., Grishko V. V., Tolstikov A. G., Voronova L. N.: Synthesis of C2 symmetric triterpene bis-enaminones. Chem Natur Comp 2012, 48, 75. <http://dx.doi.org/10.1007/s10600-012-0162-z>
  • Villemin Didier, Cheikh Nawel, Liao Liang, Bar Nathalie, Lohier Jean-François, Sopkova Jana, Choukchou-Braham Noureddine, Mostefa-Kara Bachir: Two versatile routes towards Cerpegin and analogues: applications of a one pot reaction to new analogues of Cerpegin. Tetrahedron 2012, 68, 4906. <http://dx.doi.org/10.1016/j.tet.2012.03.057>
  • Bondžić Bojan P., Džambaski Zdravko, Bondžić Aleksandra M., Marković Rade: π-Annulation reactions of 4-thiazolidinone enaminones in the synthesis of fused bi- and tri-cyclic compounds. Tetrahedron 2012, 68, 9556. <http://dx.doi.org/10.1016/j.tet.2012.09.080>
  • Liu Pengfei, Shan Gang, Chen Shi, Rao Yu: A new regio- and stereoselective synthesis of β-enamino ketones with 3-ethoxycyclobutanones and substituted amines. Tetrahetron Lett 2012, 53, 936. <http://dx.doi.org/10.1016/j.tetlet.2011.12.040>
  • Indulkar Utkarsha U., Kale Sandip R., Gawande Manoj B., Jayaram Radha V.: Ecofriendly and facile Nano ZnO catalyzed solvent-free enamination of 1,3-dicarbonyls. Tetrahedron Letters 2012, 53, 3857. <http://dx.doi.org/10.1016/j.tetlet.2012.05.048>
  • Cunha Silvio, Gomes Amenson Trindade: Synthesis of α-aryl enaminones through reactions of β-aryl enones with benzyl azide. Tetrahedron Letters 2012, 53, 6710. <http://dx.doi.org/10.1016/j.tetlet.2012.09.125>
  • Joshi Megha, Patel Monika, Tiwari Rakesh, Verma Akhilesh K.: Base-Mediated Selective Synthesis of Diversely Substituted N-Heterocyclic Enamines and Enaminones by the Hydroamination of Alkynes. J. Org. Chem. 2012, 77, 5633. <http://dx.doi.org/10.1021/jo300782n>
  • Mthembu Siyanda T., Madeley Lee G., Koning Charles B. de, Michael Joseph P.: 2-[(2Z)-Azepan-2-ylidene]-1-(4-nitrophenyl)ethanone. Acta Crystallogr E Struct Rep Online 2012, 68, o2479. <http://dx.doi.org/10.1107/S1600536812032035>
  • Madeley Lee G., Morgans Garreth L., Lemmerer Andreas, Michael Joseph P.: (2E)-1-Phenyl-2-[1-(2-phenylprop-2-en-1-yl)pyrrolidin-2-ylidene]ethanone. Acta Crystallogr E Struct Rep Online 2012, 68, o3281. <http://dx.doi.org/10.1107/S1600536812044443>
  • Ghandi Mehdi, Jameà Amir Hossein: Pyridine-mediated, one-pot, stereoselective synthesis of acyclic enaminones. Tetrahetron Lett 2011, 52, 4005. <http://dx.doi.org/10.1016/j.tetlet.2011.05.112>
  • Michael Joseph P., De Koning Charles B., Gravestock David, Hosken Gladys D., Howard Arthur S., Jungmann Christa M., Krause Rui W. M., Parsons Andrew S., Pelly Stephen C., Stanbury Trevor V.: ChemInform Abstract: Enaminones: Versatile Intermediates for Natural Product Synthesis. ChemInform 2010, 31, no. <http://dx.doi.org/10.1002/chin.200004280>
  • Randive Nitin A., Kumar Varun, Nair Vipin A.: A facile approach to substituted acrylates by regioselective and stereoselective addition of thiols and amines to an alkynyl ester in water. Monatshefte für Chemie 2010, 141, 1329. <http://dx.doi.org/10.1007/s00706-010-0399-9>
  • Timur Mahir, Kavak Gülten, Şenöz Hülya, İde Semra, Tunoğlu Nazan: Synthesis, Crystallographic and Spectral Studies of 3-(4-(Phenylamino) Phenylamino)Cyclohex-2-Enone. J Chem Crystallogr 2010, 40, 376. <http://dx.doi.org/10.1007/s10870-009-9664-3>
  • Valla Alain, Méheux Nathalie, Cartier Dominique, Valla Benoist, Dufossé Laurent, Labia Roger: Synthesis of a New C-15 Phosphorus Ylide Used for the Preparation of Some β-End-Group Retinoid Derivatives. Synth Comm 2010, 41, 184. <http://dx.doi.org/10.1080/00397910903531938>
  • Datta Bandita, Pasha M. A.: Silica Sulfuric Acid–Mediated Synthesis of β-Enaminones and β-Enaminoesters Under Microwave Irradiation. Phosphorus Sulfur Silicon Relat Elem 2010, 186, 171. <http://dx.doi.org/10.1080/10426507.2010.492365>
  • Amézquita-Valencia Manuel, Hernández-Ortega Simón, Suárez-Ortiz G. Alejandra, Cabrera Armando: (Z)-Ethyl 3-(2,6-diisopropylanilino)but-2-enoate. Acta Crystallogr E Struct Rep Online 2010, 66, o500. <http://dx.doi.org/10.1107/S1600536810003260>
  • Zhang Li-Feng, Yang Shu-Tao: Silica-supported antimony(III) chloride as an efficient heterogeneous catalyst for the synthesis of aminopropenones and 3-aminopropenoates under solvent-free conditions. Russ J Org Chem 2009, 45, 18. <http://dx.doi.org/10.1134/S1070428009010023>
  • P. Michael Joseph, B. de Koning Charles, L. Riley Darren: Formal Synthesis of (5R,8R,8aS)-Indolizidine 209I via Enaminones Incorporating Weinreb Amides. HETEROCYCLES 2009, 79, 935. <http://dx.doi.org/10.3987/COM-08-S(D)68>
  • Krishna Palakodety Radha, Sekhar Empati Raja: p-Toluenesulfonylmethyl Isocyanide (TosMIC) and Indium Manifold Strategy to Access β-Keto-(E)-enamino Esters from 1,3-Dicarbonyl Compounds. Adv Synth Catal 2008, 350, 2871. <http://dx.doi.org/10.1002/adsc.200800368>
  • Li Geng-Chen: Simple and efficient synthesis of 3-aminopropenones and 3-aminopropenoates catalyzed by copper(II) nitrate trihydrate under solvent-free conditions. Monatshefte für Chemie 2008, 139, 789. <http://dx.doi.org/10.1007/s00706-007-0832-x>
  • Dobrynin A. B., Gryaznov P. I., Naumova O. E., Litvinov I. A., Alfonsov V. A.: Crystal and molecular structures of (3Z)-(±)-4-(2′-hydroxypropyl)amino-and (3Z)-4-(2′-hydroxyethyl)amino-pent-3-en-2-ones. J Struct Chem 2008, 49, 917. <http://dx.doi.org/10.1007/s10947-008-0157-6>
  • Rafiee Ezzat, Joshaghani Mohammad, Eavani Sara, Rashidzadeh Solmaz: A revision for the synthesis of β-enaminones in solvent free conditions: efficacy of different supported heteropoly acids as active and reusable catalysts. Green Chem 2008, 10, 982. <http://dx.doi.org/10.1039/b803249a>
  • Palimkar Sanjay S., More Vijaykumar S., Srinivasan Kumar V.: Simple and Efficient One‐Pot, Three‐Component, Solvent‐Free Synthesis of β‐Enaminones via Sonogashira Coupling–Michael Addition Sequences. Synth Comm 2008, 38, 1456. <http://dx.doi.org/10.1080/00397910801914343>
  • Zhang Li-Ping, Ni Cai-Hua, Li Zhi-Yong, Zhang Wei: (Z)-Methyl 3-(4-ethoxyanilino)but-2-enoate. Acta Crystallogr E Struct Rep Online 2008, 64, o1051. <http://dx.doi.org/10.1107/S160053680800891X>
  • Zhang Li-Ping, Ni Cai-Hua, Zhang Zhan-Hui: (Z)-3-[1-(4-Methoxyanilino)ethylidene]-4,5-dihydrofuran-2(3H)-one. Acta Crystallogr E Struct Rep Online 2008, 64, o1328. <http://dx.doi.org/10.1107/S1600536808016504>
  • Zhang Li-Ping, Wei Lin-Juan, Chen Ming-Qing, Zhang Zhan-Hui: (Z)-3-Anilino-1,3-diphenylprop-2-en-1-one. Acta Crystallogr E Struct Rep Online 2008, 64, o1327. <http://dx.doi.org/10.1107/S1600536808016711>
  • Approaches to the Syntheses of Partially Reduced Imidazo[1,2-a]pyridines. Bulletin of the Korean Chemical Society 2008, 29, 1998. <http://dx.doi.org/10.5012/bkcs.2008.29.10.1998>
  • Alizadeh Abdolali, Rezvanian Atieh, Zhu Long-Guan: One-Pot Synthesis of 4-(Alkylamino)-1-(arylsulfonyl)-3-benzoyl-1,5- dihydro-5-hydroxy-5-phenyl-2H-pyrrol-2-onesvia a Multicomponent Reaction. HCA 2007, 90, 2414. <http://dx.doi.org/10.1002/hlca.200790248>
  • Vdovenko Sergey I., Gerus Igor I., Kukhar Valery P.: Steric effects on the mechanism of reaction of nucleophilic substitution of β-substituted alkoxyvinyl trifluoromethyl ketones with four secondary amines. J Phys Org Chem 2007, 20, 190. <http://dx.doi.org/10.1002/poc.1152>
  • Choudhury Anusuya, Breslav Michael, Grimm Jeffrey S., Xiao Tong, Xu Dawei, Sorgi Kirk L.: A facile one-pot synthesis of acyclic β-enamino ketones, an important class of versatile synthetic intermediates. Tetrahetron Lett 2007, 48, 3069. <http://dx.doi.org/10.1016/j.tetlet.2007.02.115>
  • Prabhakar Akundi Surya, Sashikanth Suthrapu, Reddy Padi Pratap, Cherukupally Praveen: An efficient synthesis of vinylogous carbamates from alkyl azides. Tetrahetron Lett 2007, 48, 8709. <http://dx.doi.org/10.1016/j.tetlet.2007.10.013>
  • Wang Xin, Turunen Brandon J., Leighty Matthew W., Georg Gunda I.: Microwave-assisted Suzuki–Miyaura couplings on α-iodoenaminones. Tetrahetron Lett 2007, 48, 8811. <http://dx.doi.org/10.1016/j.tetlet.2007.10.078>
  • Kumar Rishi, Maulik Prakas R., Kumar Misra Anup: Efficient Synthesis of Glycosyl Enaminoesters Directly from Glycosyl Azides*. J Carbohydr Chem 2007, 26, 83. <http://dx.doi.org/10.1080/07328300701296844>
  • Zhang Zhan-Hui, Yin Liang, Wang Yong-Mei: A General and Efficient Method for the Preparation of β-Enamino Ketones and Esters Catalyzed by Indium Tribromide. Adv Synth Catal 2006, 348, 184. <http://dx.doi.org/10.1002/adsc.200505268>
  • Das Biswanath, Venkateswarlu Katta, Majhi Anjoy, Reddy Majjigapu Ravinder, Reddy Kuravallapalli Nagabhushana, Rao Yerra Koteswara, Ravikumar Krishnan, Sridhar Balasubramanian: Highly efficient, mild and chemo- and stereoselective synthesis of enaminones and enamino esters using silica supported perchloric acid under solvent-free conditions. Journal of Molecular Catalysis A 2006, 246, 276. <http://dx.doi.org/10.1016/j.molcata.2005.11.045>
  • Alizadeh Abdolali, Movahedi Farnaz, Esmaili Abbas Ali: A new method for the synthesis of functionalized maleimides. Tetrahetron Lett 2006, 47, 4469. <http://dx.doi.org/10.1016/j.tetlet.2006.04.040>
  • Reddy D. Srinivasa, Rajale Trideep V., Shivakumar K., Iqbal Javed: A mild and efficient method for the synthesis of vinylogous carbamates from alkyl azides. Tetrahetron Lett 2005, 46, 979. <http://dx.doi.org/10.1016/j.tetlet.2004.12.047>
  • Valla Alain, Valla Benoist, Cartier Dominique, Le Guillou Régis, Labia Roger, Potier Pierre: New aromatic annulation reaction via a C14 enaminone synthon: synthesis of ‘terpenoid-like chalcones’. Tetrahetron Lett 2005, 46, 6671. <http://dx.doi.org/10.1016/j.tetlet.2005.07.141>
  • Bélanger Guillaume, Larouche-Gauthier Robin, Ménard Frédéric, Nantel Miguel, Barabé Francis: Addition of Tethered Nonaromatic Carbon Nucleophiles to Chemoselectively Activated Amides. Org Lett 2005, 7, 4431. <http://dx.doi.org/10.1021/ol0516519>
  • Michael Joseph P., de Koning Charles B., van der Westhuyzen Christiaan W.: Studies towards the enantioselective synthesis of 5,6,8-trisubstituted amphibian indolizidine alkaloids via enaminone intermediates. Org Biomol Chem 2005, 3, 836. <http://dx.doi.org/10.1039/b418062c>
  • Zhao Yuanhong, Zhao Jingfeng, Zhou Yongyun, Lei Ze, Li Liang, Zhang Hongbin: Efficient synthesis of β-amino-α,β-unsaturated carbonyl compounds. New J Chem 2005, 29, 769. <http://dx.doi.org/10.1039/b419254k>
  • Vohra Ramandeep Kaur, Renaud Jean-Luc, Bruneau Christian: Efficient Synthesis of β-Aminoacrylates and β-Enaminones Catalyzed by Zn(OAc)2·2H2O. Collect Czech Chem Commun 2005, 70, 1943. <http://dx.doi.org/10.1135/cccc20051943>
  • Negri Giuseppina, Kascheres Concetta, Kascheres Albert J.: Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds. Journal of Heterocyclic Chemistry 2004, 41, 461. <http://dx.doi.org/10.1002/jhet.5570410402>
  • Khosropour Ahmad R., Khodaei Mohammad M., Kookhazadeh Mehdi: A mild, efficient and environmentally friendly method for the regio- and chemoselective synthesis of enaminones using Bi(TFA)3 as a reusable catalyst in aqueous media. Tetrahetron Lett 2004, 45, 1725. <http://dx.doi.org/10.1016/j.tetlet.2003.12.093>
  • Robinson Ross S., Dovey Martin C., Gravestock David: Silver-catalysed hydroamination: synthesis of functionalised pyrroles. Tetrahetron Lett 2004, 45, 6787. <http://dx.doi.org/10.1016/j.tetlet.2004.07.019>
  • Lyutenko Natalie V, Gerus Igor I, Kacharov Alexey D, Kukhar Valery P: Regioselective reactions of β-aminovinyl trifluoromethyl ketones with tosyl isocyanate. Tetrahedron 2003, 59, 1731. <http://dx.doi.org/10.1016/S0040-4020(03)00106-6>
  • Reddy D. Srinivasa, Judd Weston R., Aubé Jeffrey: Lewis Acid-Mediated Reactions of Alkyl Azides with α,β-Unsaturated Ketones. Org Lett 2003, 5, 3899. <http://dx.doi.org/10.1021/ol0355130>
  • Michael Joseph P, de Koning Charles B, Hosken Gladys D, Stanbury Trevor V: Reformatsky reactions with N-arylpyrrolidine-2-thiones: synthesis of tricyclic analogues of quinolone antibacterial agents. Tetrahedron 2001, 57, 9635. <http://dx.doi.org/10.1016/S0040-4020(01)00964-4>
  • Michael Joseph P, de Koning Charles B, Petersen Riaan L, Stanbury Trevor V: Asymmetric synthesis of a tetracyclic model for the aziridinomitosenes. Tetrahetron Lett 2001, 42, 7513. <http://dx.doi.org/10.1016/S0040-4039(01)01597-0>
  • Ma Dawei, Zhu Wei: Two-Component Method to Enantiopure Quinolizidinones and Indolizidinones. Total Synthesis of (−)-Lasubine II. Org Lett 2001, 3, 3927. <http://dx.doi.org/10.1021/ol016802w>