A First Resource-Efficient and Highly Flexible Procedure for a Four-Component Synthesis of Dispiropyrrolidines

Two series of dispiropyrrolidine derivatives were successfully synthesized by a tandem Knoevenagel–1,3-dipolar cycloaddition reaction sequence of isatin or acenaphthylene-1,2-dione, sarcosine, 1,3-indanedione, and an aldehyde without any catalyst. This strategy is not only suitable to aromatic aldehydes but aliphatic and heteroaromatic aldehydes as well. Moreover, this one-pot, four-component synthesis of dispiropyrrolidines is the first of its kind, as the dipole azomethine ylide and dipolarophile can be generated in situ. Such a strategy would provide access to a fast one-pot synthesis of dispiroheterocycles, which are otherwise accessible only through multistep synthesis. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

[1]  Shusheng Zhang,et al.  Application of beta-(2-chloroaroyl) thioacetanilides in synthesis: an unusual and highly efficient access to thiochromeno[2,3-b]pyridine derivatives. , 2008, The Journal of organic chemistry.

[2]  S. Perumal,et al.  Sacrificial azomethine ylide cycloaddition controlled chemoselective nitrile oxide cycloaddition to 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: formation of mono-spiro-isoxazolines , 2007 .

[3]  A. Padwa,et al.  The Synthesis of Heterocycles Using Cascade Chemistry , 2007 .

[4]  Yong‐Min Liang,et al.  New light on an old story: facile and efficient synthesis of 1,3-diaryl-5-spirohexahydropyrimidines via a six-molecule, three-component mannich-type reaction. , 2007, The Journal of organic chemistry.

[5]  P. Shanmugam,et al.  Synthesis of novel functionalized 3-spiropyrrolizidine and 3-spiropyrrolidine oxindoles from Baylis-Hillman adducts of isatin and heteroaldehydes with azomethine ylides via [3+2]-cycloaddition. , 2007, Organic letters.

[6]  Ming Li,et al.  Ionic liquid phase synthesis of tetrahydropyrano- and tetrahydrofuranoquinolines under microwave irradiation. , 2007, Journal of combinatorial chemistry.

[7]  A. Padwa,et al.  The Domino Way to Heterocycles. , 2007, Tetrahedron.

[8]  L. Neuville,et al.  Palladium-catalyzed three-component synthesis of 3-(diarylmethylene)oxindoles through a domino Sonagashira/carbopalladation/C--H activation/C--C bond-forming sequence. , 2007, Angewandte Chemie.

[9]  H. Pellissier.  Asymmetric 1,3-Dipolar Cycloadditions , 2007 .

[10]  Jieping Zhu,et al.  Modulating the reactivity of alpha-isocyanoacetates: multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones. , 2007, Angewandte Chemie.

[11]  N. Fujii,et al.  Direct synthesis of 2-(aminomethyl)indoles through copper(I)-catalyzed domino three-component coupling and cyclization reactions. , 2007, Angewandte Chemie.

[12]  R. Raghunathan,et al.  ZrOCl2·8H2O mediated microwave induced [3+2] cycloaddition of azomethine ylides—a facile one-pot synthesis of novel dispiroheterocycles , 2007 .

[13]  Kanumuri Ramesh Reddy,et al.  Simple and one-pot protocol for synthesis of indene-spiro-oxindoles involving tandem Prins and Friedel-Crafts reactions. , 2007, Organic letters.

[14]  K C Nicolaou,et al.  Cascade reactions in total synthesis. , 2006, Angewandte Chemie.

[15]  S. Gadre,et al.  Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides. , 2006, Chemical reviews.

[16]  Ming Li,et al.  One-pot synthesis of Biginelli and Hantzsch products catalyzed by non-toxic ionic liquid (BMImSac) and structural determination of two products , 2006 .

[17]  J. Ohshita,et al.  CO2 incorporation reaction using arynes: straightforward access to benzoxazinone. , 2006, Journal of the American Chemical Society.

[18]  Frédéric Liéby-Muller,et al.  Current Developments in Michael Addition-Based Multicomponent Domino Reactions Involving 1,3-Dicarbonyls and Derivatives , 2006 .

[19]  Su Qiu,et al.  Structure-based design of spiro-oxindoles as potent, specific small-molecule inhibitors of the MDM2-p53 interaction. , 2006, Journal of medicinal chemistry.

[20]  B. Arndtsen,et al.  A direct, one step synthesis of imidazoles from imines and acid chlorides: a palladium catalyzed multicomponent coupling approach. , 2006, Journal of the American Chemical Society.

[21]  Shinsuke Komagawa,et al.  Nickel-catalyzed three-component [3+2+2] cocyclization of ethyl cyclopropylideneacetate and alkynes-selective synthesis of multisubstituted cycloheptadienes. , 2006, Angewandte Chemie.

[22]  Susumu Kobayashi,et al.  Highly diastereoselective one-pot synthesis of spirocyclic oxindoles through intramolecular Ullmann coupling and Claisen rearrangement. , 2006, Angewandte Chemie.

[23]  H. Pellissier.  Asymmetric domino reactions. Part B: Reactions based on the use of chiral catalysts and biocatalysts , 2006 .

[24]  H. Pellissier.  Asymmetric domino reactions. Part A: Reactions based on the use of chiral auxiliaries , 2006 .

[25]  A. Amani,et al.  (S)-Proline as a Neutral and Efficient Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives in Aqueous Media , 2006 .

[26]  E. Suresh,et al.  N-Heterocyclic Carbene Catalyzed Reaction of Enals and 1,2-Dicarbonyl Compounds: Stereoselective Synthesis of Spiro γ-Butyrolactones , 2006 .

[27]  C. Fishwick,et al.  Stereoselective palladium-catalyzed four-component cascade synthesis of pyrrolidinyl-, pyrazolidinyl-, and isoxazolidinyl isoquinolines. , 2005, Angewandte Chemie.

[28]  B. Skelton,et al.  Synthesis of 2-azaspiro[4.4]nonan-1-ones via phosphine-catalysed [3+2]-cycloadditions , 2005 .

[29]  Xinhua Duan,et al.  Palladium-catalyzed one-pot synthesis of highly substituted furans by a three-component annulation reaction. , 2005, The Journal of organic chemistry.

[30]  I. Coldham,et al.  Intramolecular dipolar cycloaddition reactions of azomethine ylides. , 2005, Chemical reviews.

[31]  R. Raghunathan,et al.  A regioselective synthesis of dispiro[oxindole-cyclohexanone]pyrrolidines and dispiro[oxindole-hexahydroindazole]pyrrolidines by sequential 1,3-dipolar cycloaddition and annulation through a microwave induced solvent-free approach , 2005 .

[32]  K. Rück-Braun,et al.  1,3-dipolar cycloaddition on solid supports: nitrone approach towards isoxazolidines and isoxazolines and subsequent transformations. , 2005, Chemical Society reviews.

[33]  Jieping Zhu,et al.  Multicomponent Reactions: ZHU:MULTICOMPONENT REACTIONS O-BK , 2005 .

[34]  S. Schreiber,et al.  A library of spirooxindoles based on a stereoselective three-component coupling reaction. , 2004, Journal of the American Chemical Society.

[35]  C. Barbas,et al.  Towards organo-click chemistry: development of organocatalytic multicomponent reactions through combinations of aldol, Wittig, Knoevenagel, Michael, Diels-Alder and Huisgen cycloaddition reactions. , 2004, Chemistry.

[36]  A. Karimi,et al.  A novel four-component reaction for the diastereoselective synthesis of some new spiro pyrrolizidines via 1,3-dipolar cycloaddition of azomethine ylides , 2004 .

[37]  R. Raghunathan,et al.  A facile synthesis of novel dispiroheterocycles through solvent-free microwave-assisted [3+2] cycloaddition of azomethine ylides , 2004 .

[38]  M. Lautens,et al.  Palladium-catalyzed sequential alkylation-alkenylation reactions: new three-component coupling leading to oxacycles. , 2003, Organic letters.

[39]  J. Sansano,et al.  Azomethine Ylides in Organic Synthesis , 2003 .

[40]  F. Clerici,et al.  A new synthetic procedure to spiro[cyclohexane-1,3′-indoline]-2′,4-diones , 2003 .

[41]  E. Carreira,et al.  Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids , 2003 .

[42]  L. Overman,et al.  Catalytic asymmetric synthesis of quaternary carbons bearing two aryl substituents. Enantioselective synthesis of 3-alkyl-3-aryl oxindoles by catalytic asymmetric intramolecular heck reactions. , 2003, Journal of the American Chemical Society.

[43]  R. Raghunathan,et al.  A facile entry into a new class of spiroheterocycles: synthesis of dispiro[oxindolechromanone/flavanone/tetralone]pyrroloisoquinoline ring systems , 2002 .

[44]  S. Kanemasa.  Metal-Assisted Stereocontrol of 1,3-Dipolar Cycloaddition Reactions , 2002 .

[45]  B. List.  Proline-catalyzed asymmetric reactions , 2002 .

[46]  A. Padwa,et al.  Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products , 2002 .

[47]  C. Barbas,et al.  A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids , 2002 .

[48]  T. Kawabata,et al.  Total synthesis of spirotryprostatin B via asymmetric nitroolefination. , 2002, Organic letters.

[49]  A. A. Raj,et al.  A Novel Entry into a New Class of Spiroheterocyclic Framework: Regioselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines and Dispiro[oxindolehexahydroindazole]pyrrolidines. , 2001 .

[50]  R. Grigg,et al.  Sequential decarboxylative azomethine ylide cycloaddition—palladium catalysed hydrostannylation–cyclisation-anion capture processes , 2001 .

[51]  H. Högberg,et al.  ASYMMETRIC 1,3-DIPOLAR CYCLOADDITIONS FOR THE CONSTRUCTION OF ENANTIOMERICALLY PURE HETEROCYCLES. A REVIEW , 2001 .

[52]  S. Hilton,et al.  A new route to spirooxindoles. , 2000, Organic letters.

[53]  H. Fun,et al.  Photoinduced reactions of 1-acetylisatin with phenylacetylenes. , 2000, Organic letters.

[54]  James L. Melville,et al.  A new Claisen sequence for the synthesis of 3-substituted-2-oxindoles , 2000 .

[55]  Robert M. Williams,et al.  The Asymmetric Total Synthesis of (+)- and (−)-Spirotryprostatin B , 2000 .

[56]  G. Olah,et al.  Preparation of 3,3-Diaryloxindoles by Superacid-Induced Condensations of Isatins and Aromatics with a Combinatorial Approach , 1998 .

[57]  K. Gothelf,et al.  Asymmetric 1,3-Dipolar Cycloaddition Reactions. , 1998, Chemical reviews.

[58]  H. Kakeya,et al.  Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase☆ , 1997 .

[59]  L. Tietze.  Domino Reactions in Organic Synthesis. , 1996, Chemical reviews.

[60]  R. Bunce.  Recent advances in the use of tandem reactions for organic synthesis , 1995 .

[61]  R. Huisgen,et al.  Regiochemistry in cycloadditions of diazomethane to thioformaldehyde and thioketones , 1993 .

[62]  R. Bridges,et al.  Conformationally restricted inhibitors of the high affinity L-glutamate transporter , 1993 .

[63]  T. Ho.  Tandem Organic Reactions , 1992 .

[64]  R. Huisgen,et al.  Stereochemistry of tetracyanoethylene cycloadditions to thioenol ethers , 1979 .

[65]  M. Abou-Gharbia,et al.  Synthesis of Tricyclic Arylspiro Compounds as Potential Antileulemic and Anticonvulsant Agents , 1979 .

[66]  M. Kornet,et al.  Oxindole-3-spiropyrrolidines and -piperidines. Synthesis and local anesthetic activity. , 1976, Journal of medicinal chemistry.

[67]  A. Peters,et al.  Synthesis and antiviral activities of adamantane spiro compounds. 1. Adamantane and analogous spiro-3'-pyrrolidines. , 1972, Journal of medicinal chemistry.