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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 11
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Synthetic Communications Reviews

Chemistry of 3-(1H-Indol-3-yl)-3-oxopropanenitrile

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Pages 1579-1599 | Received 29 Oct 2013, Published online: 14 May 2014

REFERENCES

  • Houlihan , W. J. ; Remers , W. A. ; Brown , R. K. Indoles: Part I ; Wiley : New York , 1992 .
  • Sundberg , R. J. The Chemistry of Indoles ; Academic Press : New York , 1996 .
  • (a) Casapullo , A. ; Bifulco , G. ; Bruno , I. ; Riccio , R. New bisindole alkaloids of the topsentin and hamacanthin classes from the Mediterranean marine sponge Rhaphisia lacazei . J. Nat. Prod. 2000 , 63 , 447 – 451 ; (b) Bao , B. ; Sun , Q. ; Yao , X. ; Hong , J. ; Lee , C. O. ; Sim , C. J. ; Im , K. S. ; Jung , J. H. Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp . J. Nat. Prod. 2005 , 68 , 711 – 715 .
  • Skibo , E. B. ; Xing , C. ; Dorr , R. T. Aziridinyl quinone antitumor agents based on indoles and cyclopent[b]indoles: Structure–activity relationships for cytotoxicity and antitumor activity . J. Med. Chem. 2001 , 44 , 3545 – 3562 .
  • Gupta , L. ; Talwar , A. ; Palne , N. S. ; Gupta , S. ; Chauhan , P. M. S. Design, synthesis, and SAR of macrocyclic tertiary carbinamine BACE-1 inhibitors . Bioorg. Med. Chem. Lett. 2007 , 17 , 4057 – 4061 .
  • Smith , G. F. Indole is an important heterocycle, both in nature as well as for commercial drug . Adv. Heterocycle. Chem. 1963 , 2 , 300 – 309 .
  • Ishii , H. ; Murakami , K. ; Murakami , Y. ; Hosoya , K. Fischer indolization and its related compounds, XI: New indole trimer . Chem. Pharm. Bull. 1977 , 25 , 3122 – 3124 .
  • Bergman , J. ; Backvall , J. E. ; Lindstrom , J. O. Synthesis and reactions of some 3-(2-haloacyl)indoles . Tetrahedron 1973 , 29 , 971 – 976 .
  • Bergman , J. ; Bergman , S. ; Lindström , J.-O. Oxidation of methyl indole-3-acetate induced by FeCl3 and secondary amines . Tetrahedron Lett. 1989 , 30 , 5337 – 5340 .
  • Ottoni , O. ; Neder , V. F. ; Dias , A. K. B. ; Cruz , R. P. A. ; Aquino , L. B. Acylation of indole under Friedel–Crafts conditions: An improved method to obtain 3-acylindoles regioselectively . Org. Lett. 2001 , 3 , 1005 – 1007 .
  • Hayashi , H. ; Ohmoto , S. ; Somei , M. The first syntheses of antiviral, cytotoxic 6-cyano-5-methoxy- and -12-methylindolo[2,3-a]carbazoles, and related indolo[2,3-a]carbazoles from indigo . Heterocycl. 1997 , 45 , 1647 – 1650 .
  • Eby , C. J. ; Hauser , C. R. Acylations of nitriles with esters by sodium amide in liquid ammonia to form β-ketonitriles: Consideration of amidine formation . J. Am. Chem. Soc. 1957 , 79 , 723 – 725 .
  • Freidrich Bayer & Co. Patent 175415, 1905 ; Chem. Abstr. 1905 , 1 , 6240 .
  • Papesch , V. ; Schroeder , E. Synthesis of 1-mono- and 1,3-di-substituted 6-aminouracils: Diuretic activity . J. Org. Chem. 1951 , 16 , 1879 – 1890 .
  • Okauchi , T. ; Itonaga , M. ; Minami , T. ; Owa , T. ; Kitoh , K. ; Yoshino , H. A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminum chloride . Org. Lett. 2000 , 2 , 1485 – 1487 .
  • Isobe , Y. ; Tobe , M. ; Inoue , Y. ; Isobe , Y. ; Tsuchiya , M. ; Hayashi , H. Structure and activity relationships of novel uracil derivatives as topical anti-inflammatory agents . Bioorg. Med. Chem. 2003 , 11 , 4933 – 4940 .
  • Kaniwa , K. ; Arai , M. A. ; Li , X. ; Ishibashi , M. Synthesis, determination of stereochemistry, and evaluation of new bisindole alkaloids from the myxomycete Arcyria ferruginea: An approach for Wnt signal inhibitor . Bioorg. Med. Chem. Lett. 2007 , 17 , 4254 – 4257 .
  • Slaett , J. ; Romero , I. ; Bergman , J. Cyanoacetylation of indoles, pyrroles, and aromatic amines with the combination cyanoacetic acid and acetic anhydride. Synthesis 2004, 16, 2760–2765.
  • Al-Awadi , N. A. ; Abdelkhalik , M. M. ; Abdelhamid , I. A. ; Elnagdi , M. H. Pyrolytic methods in organic synthesis: Novel routes for the synthesis of 3-oxoalkanenitriles, 2-acyl anilines, and 2-aroyl anilines . Synlett 2007 , 19 , 2979 – 2982 .
  • Abdallah , T. A. Studies with enamines and azaenamines: Synthesis and reactivity of 3-dimethylamino-2-[(3-indolyl) carbonyl]propenonitrile . J. Heterocycl. Chem. 2007 , 44 , 961 – 965 .
  • Kreher , R. ; Wagner , P. H. Notiz zur cyanacetylierung von pyrrolen und indolen . Chem. Ber. 1980 , 113 , 3675 – 3677 .
  • Stetinova , J. ; Kada , R. ; Lesko , J. ; Zalibera , L. ; Ilavsky , D. ; Bartovic , A. Collect. Czech Chem. C 1995 , 60 , 999 .
  • Al-Lohedan , H. ; Bunton , C. A. Micellar effects upon the ElcB mechanism of ester hydrolysis . J. Org. Chem. 1981 , 46 , 3929 – 3930 .
  • Suvorov , N. N. ; Kholodkovskaya , K. B. ; Preobrazhenskaya , M. N. Indole derivatives, XXIII: 3-Indolylethylene glycol . Chem. Heterocycl. Compd. Engl. Transl. 1965 , 2 , 265 – 270 ; Chem. Abstr. 1966 , 63 , 38963 .
  • Song-Lei , Z. ; Shun-Jun , J. ; Xiao-Ming , S. ; Chang , S. ; Yu , L. Facile and efficient synthesis of a new class of bis(3′-indolyl)pyridine derivatives via one-pot multicomponent reactions . Tetrahedron Lett. 2008 , 49 , 1777 – 1781 .
  • Bergman , J. ; Koch , E. ; Pelcman , B. 2,2′-Biindolyl revisited: Synthesis and reactions . Tetrahedron 1995 , 51 , 5631 – 5642 .
  • Baker , J. W. Syntheses in the indole series, part II: Derivatives of β-keto-β-3-indolylpropionic acid . Chem. Soc. 1964 , 461 – 463 .
  • Cai , X. ; Snieckus , V. Combined directed ortho and remote metalation–cross-coupling strategies: General method for benzo[a]carbazoles and the synthesis of an unnamed indolo[2,3-a]carbazole alkaloid . Org. Lett. 2004 , 6 , 2293 – 2295 .
  • Majima , R. ; Hoshino , T. Synthetische versuche in der indol-gruppe, VI: Eine neue synthese von β-indolyl-alkylaminen . Chem. Ber. 1925 , 58 , 2042 – 2046 .
  • Gompper , R. ; Topfl , W. Carbonsäurederivate, V: Substituierte dithiocarbonsäuren und ketenmercaptale . Chem. Ber. 1962 , 95 , 2861 – 2870 .
  • Slaett , J. ; Janosik , T. ; Wahlstroem , N. ; Bergman , J. Synthetic applications of 3-(cyanoacetyl)indoles and related compounds . J. Heterocycl. Chem. 2005 , 42 , 141 – 145 .
  • Siena Biotech , S. P. A. Wyeth Pharmaceuticals. WO Patent 2008/87529 (2008) , (A1) .
  • Abdel-Motaleb , R. M. ; Makhloof , A. A. ; Ibrahim , H. M. ; Elnagdi , M. H. Studies with azoles and benzoazoles: A novel simple approach for synthesis of 3-functionally substituted 3-acylindoles . J. Heterocycl. Chem. 2007 , 44 , 109 – 114 .
  • Radwan , M. A. A. ; Ragab , E. A. ; Sabry , N. M. ; El-Shenawy , S. M. Synthesis and biological evaluation of new 3-substituted indole derivatives as potential anti-inflammatory and analgesic agents . Bioorg. Med. Chem. 2007 , 15 , 3832 – 3841 .
  • Sheehan , J. C. ; Mania , D. ; Nakamura , S. ; Stock , J. A. ; Maeda , K. The structure of telomycin . J. Am. Chem. Soc. 1968 , 90 , 462 – 470 .
  • Pietra , F. Seven-membered conjugated carbo- and heterocyclic compounds and their homoconjugated analogs and metal complexes: Synthesis, biosynthesis, structure, and reactivity . Chem. Rev. 1973 , 73 , 293 – 364 .
  • Galvez , J. ; Quiroga , J. ; Cobo , J. ; Low , J. N. ; Glidewell , C. (E)-3-Dimethylamino-2-(1H-indol-3-ylcarbonyl)acrylonitrile: A chain of edge-fused rings built from a three-centre N—H…(N,O) hydrogen bond . Acta Crystal., Section C: Crystal Structure Commun. 2008 , 64 , 385 – 387 .
  • Abdallah , T. A. Studies with enamines and azaenamines: Synthesis and reactivity of 3-dimethylamino-2-[(3-indolyl) carbonyl]propenonitrile. J. Heterocycl. Chem. 2007, 44, 961–965.
  • Anderson , L. ; Zhou , M. ; Santiago , D. N. ; Guida , W. C. ; Mclaughlin , M. L. ; Sharma , V. ; Mclaughlin , J. M. ; Fronczek , F. R. Facile iterative synthesis of 2,5-terpyrimidinylenes as nonpeptidic α-helical mimics . J. Org. Chem. 2010 , 75 , 4288 – 4291 .
  • Radwan , M. A. A. ; El-Sherbiny , M. Synthesis and antitumor activity of indolylpyrimidines: Marine natural product meridianin D analogues . Bioorg. Med. Chem. 2007 , 15 , 1206 – 1211 .
  • Pokhodylo , N. T. ; Matiychuk , V. S. ; Obushak , M. D. Synthesis of triazoles via regioselective reactions of aryl azides with cyanoacetyl pyrroles and indoles . Synthesis 2009 , 8 , 1297 – 1300 .
  • Domling , A. Isocyanide-based multicomponent reactions in combinatorial chemistry . Comb. Chem. High Throughput Screen. 1998 , 1 , 1 – 22 .
  • Bazgir , A. ; Amani , V. ; Khavasi , H. R. Methyl N-[(2-hydroxynaphthalen-1-yl)(phenyl)methyl]carbamate . Acta Cryst. 2006 , E62 , 3533 – 3534 .
  • Weber , L. Multi-component reactions and evolutionary chemistry . Drug Discov. Today 2002 , 7 , 143 – 147 .
  • Zhu , J. ; Bienayme , H. Multicomponent Reactions ; Wiley-VCH : Weinheim , Germany , 2005 .
  • Wipf , P. ; Kendall , C. Novel applications of alkenyl zirconocenes . Chem. Eur. J. 2002 , 8 , 1779 – 1784 .
  • Balme , G. ; Bossharth , E. ; Monteiro , N. Pd-Assisted multicomponent synthesis of heterocycles . Eur. J. Org. Chem. 2003 , 4101 – 4111 .
  • Jacobi von Wangelin , A. ; Neumann , H. ; Gordes , D. ; Klaus , S. ; Strubing , D. ; Beller , M. Multicomponent coupling reactions for organic synthesis: Chemoselective reactions with amide–aldehyde mixtures . Chem. Eur. J. 2003 , 9 , 4286 – 4294 .
  • (a) Domling , A. ; Ugi , I. Multicomponent reactions with isocyanides . Angew. Chem., Int. Ed. 2000 , 39 , 3168 – 3210 ; (b) Heck , S. ; Domling , A. A versatile multi-component one-pot thiazole synthesis . Synlett 2000 , 424 – 426 .
  • Weber , L. The application of multi-component reactions in drug discovery . Curr. Med. Chem. 2002 , 9 , 2085 – 2093 .
  • Domling , A. Recent advances in isocyanide-based multicomponent chemistry . Curr. Opin. Chem. Biol. 2002 , 6 , 306 – 313 .
  • Zhu , J. Recent developments in the isonitrile-based multicomponent synthesis of heterocycles . Eur. J. Org. Chem. 2003 , 1133 – 1144 .
  • Sun , C. ; Ji , S. J. ; Liu , Y. Facile synthesis of 3-(2-furanyl)indoles via a multicomponent reaction . Tetrahedron Lett. 2007 , 48 , 8987 – 8989 .
  • Shaabani , A. ; Teimouri , M. B. ; Bijanzadeh , H. R. One-pot three-component condensation reaction in water: An efficient and improved procedure for the synthesis of furo[2,3-d]pyrimidine-2,4(1H,3H)-diones . Tetrahedron Lett. 2002 , 43 , 9151 – 9154 .
  • Zhu , S. L. ; Ji , S. J. ; Zhao , K. ; Liu , Y. Multicomponent reactions for the synthesis of new 3′-indolyl substituted heterocycles under microwave irradiation . Tetrahedron Lett. 2008 , 49 , 2578 – 2582 .
  • Quiroga , J. ; Trilleras , J. ; Sanchez , A. I. ; Insuasty , B. ; Abonia , R. ; Nogueras , M. Cobo , J. Regioselective three-component synthesis of indolylpyrazolo[3,4-b]pyridines induced by microwave and under solvent-free conditions . Lett. Org. Chem. 2009 , 6 , 381 – 383 .
  • Low , J. N. ; Cobo , J. ; Sanchez , A. ; Trilleras , J. ; Glidewell , C. Supramolecular aggregation in three 4-aryl-6-(1H-indol-3-yl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles . Acta Crystallograph., Sect. C 2007 , 63 , 287 – 291 .
  • Quiroga , J. ; Sanchez , A. ; Cobo , J. ; Glidewell , C. 4-(2-Fluorophenyl)-6-(1H-indol-1-yl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile: A chain of rings built from N—H…N, C—H…N and C—H…π(arene) hydrogen bonds. Acta Crystallograph., Sect. C 2009, 65, 374–376.
  • (a) Quiroga , J. ; Insuasty , B. ; Hormaza , A. ; Gamenara , D. ; Domınguez , L. ; Saldana , J. Synthesis of 5-cyanopyrazolo[3,4-b]pyridines in the reaction of 5-amino-3-methyl-1-phenylpyrazole with arylidene derivatives of malonodinitrile and ethyl cyanoacetate . J. Heterocycl. Chem. 1999 , 36 , 1311 – 1316 ; (b) Quiroga , J. ; Cruz , S. ; Insuasty , B. ; Abonia , R. ; Nogueras , M. ; Sanchez , A. ; Cobo , J. ; Low , J. N. Synthesis and structural analysis of 5-cyanodihydropyrazolo[3,4-b]pyridines . J. Heterocycl. Chem. 2001 , 38 , 53 – 60 ; (c) Zhu , S. L. ; Tu , S. J. ; Li , T. J. ; Zhang , X. J. ; Ji , S. J. ; Zhang , Y. Synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenylpyridino[2,3-c]pyrazole under microwave irradiation . Chin. J. Org. Chem. 2005 , 25 , 987 – 990 .
  • Zhao , K. ; Xu , X. P. ; Zhu , S. L. ; Shi , D. Q. ; Zhang , Y. ; Ji , S. J. Facile and efficient synthesis of a new class of indole-substituted pyridine derivatives via one-pot multicomponent reactions . Synthesis 2009 , 16 , 2697 – 2708 .
  • Thirumurugan , P. ; Perumal , P. T. A simple one-pot synthesis of functionalised 6-(indol-3-yl)-2,2′-bipyridine derivatives via multi-component reaction under neat condition . Tetrahedron Lett. 2009 , 50 , 4145 – 4150 .
  • Thirumurugan , P. ; Nandakumar , A. ; Muralidharan , D. ; Perumal , P. T. Simple and convenient approach to the Kr€ohnke pyridine type: Synthesis of functionalized indol-3-yl pyridine derivatives using 3-cyanoacetyl indole . J. Comb. Chem. 2010 , 12 , 161 – 167 .
  • Geng , L. J. ; Yu , J. G. ; Feng , G. L. Microwave-assisted synthesis of 3-cyano-2-(1H-indol-3-yl)pyridine derivatives by a multicomponent reaction . J. Chem. Res. 2010 , 6 , 333 – 335 .
  • Geng , L. J. ; Yu , J. G. ; Feng , G. L. Synthesis of 2-(1H-indol-3-yl)pyridine derivatives through multicomponent reaction . J. Chem. Res. 2010 , 10 , 565 – 567 .
  • Thirumurugan , P. ; Perumal , P. T. InCl3-mediated one-pot synthesis of indol-3-yl pyridine and 2,2′-bipyridine derivatives through multi-component reaction . Tetrahedron 2009 , 65 , 7620 – 7629 .
  • Neelakandan , V. L. ; Prakasam , T. K. M. N. ; Paramasivan , T. P. InCl3-mediated one-pot multicomponent synthesis, anti-microbial, antioxidant, and anticancer evaluation of 3-pyranyl indole derivatives . Bioorg. Med. Chem. Lett. 2010 , 20 , 5054 – 5061 .
  • Tao Chen , X. P. X. ; Shun-Jun , J. Novel, one-pot, three-component route to indole-3-yl substituted spirooxindole derivatives . J. Comb. Chem. 2010 , 12 , 659 – 663 .
  • Nandakumar , A. ; Prakasam , T. ; Paramasivan , T. P. ; Vembu , P. ; Ponnuswamy , M. N. ; Ramesh , P. One-pot multicomponent synthesis and anti-microbial evaluation of 2′-(indol-3-yl)-2-oxospiro(indoline-3,4′-pyran) derivatives . Bioorg. Med. Chem. Lett. 2010 , 20 , 4252 – 4258 .
  • Zhao , K. ; Zhu , S. L. ; Shi , D. Q. ; Xu , X. P. ; Ji , S. J. Regioselective synthesis of highly functionalized 3-spiropyrrolidine/pyrrolizidine oxindoles and acenaphthenones via one-pot four-component [3+2] cycloaddition . Synthesis 2010 , 11 , 1793 – 1803 .

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