Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 45, 2015 - Issue 20
518
Views
5
CrossRef citations to date
0
Altmetric
Synthetic Communications Reviews

Chemistry of 3-(2-Haloacyl)indoles

Pages 2271-2302 | Received 28 Apr 2015, Published online: 15 Jul 2015

REFERENCES

  • Misra, U.; Hitkari, A.; Saxena, A. K.; Gurtu, S.; Shanker, K. Biologically active indolylmethyl-1,3,4-oxadiazoles, 1,3,4-thiadiazoles, 4H-1,3,4-triazoles, and 1,2,4-triazines. Eur. J. Med. Chem. 1996, 31, 629–634.
  • Andreani, A.; Rambaldi, M.; Locatelli, A.; Pifferi, G. Synthesis and anti-inflammatory activity of indolylacrylic and methylacrylic acids. Eur. J. Med. Chem. 1994, 29, 903–906.
  • Joule, J. A. Indole and its derivatives. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; E. J. Thomas (Ed.); George Thieme Verlag: Stuttgart, Germany, 2000; Vol. 10, Chapter 10.13.
  • Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970.
  • Sundberg, R. J. In Best Synthetic Methods, Indoles; Academic Press: New York, 1996.
  • Karthikeyan, S. V.; Perumal, S.; Shetty, K. A.; Yogeeswari, P.; Sriram, D. A microwave-assisted facile regioselective Fischer indole synthesis and antitubercular evaluation of novel 2-aryl-3,4-dihydro-2H-thieno[3,2-b]indoles. Bioorg. Med. Chem. Lett. 2009, 19, 3006–3009.
  • Lakshmi, N. V.; Thirumurugan, P.; Noorulla, K. M.; Perumal, P. T. 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.
  • Giampieri, M.; Balbi, A.; Mazzei, M.; Colla, P. L.; Ibba, C.; Loddo, R. Antiviral activity of indole derivatives. Antiviral Res. 2009, 83, 179–185.
  • Agarwal, A.; Srivastava, K.; Puri, S. K.; Chauhan, P. M. S. Synthesis of substituted indole derivatives as a new class of antimalarial agents. Bioorg. Med. Chem. Lett. 2005, 15, 3133–3136.
  • Al-Qawasmeh, R. A.; Huesca, M.; Nedunuri, V.; Peralta, R.; Wright, J.; Lee, Y.; Young, A. Potent antimicrobial activity of 3-(4,5-diaryl-1H-imidazol-2-yl)-1H-indole derivatives against methicillin-resistant Staphylococcus aureus. Bioorg. Med. Chem. Lett. 2010, 20, 3518–3520.
  • Sun, C.; Ji, S.; Liu, Y. Facile synthesis of 3-(2-furanyl)indoles via a multicomponent reaction. Tetrahedron Lett. 2007, 48, 8987–8989.
  • Xiong, W. N.; Yang, C. G.; Jiang, B. Synthesis of novel analogues of marine indole alkaloids: Mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines as potential anticancer agents. Bioorg. Med. Chem. 2001, 9, 1773–1780.
  • Thirumurugan, P.; Nandakumar, A.; Muralidharan, D.; Perumal, P. T. Simple and convenient approach to the krcohnke pyridine type: Synthesis of functionalized indol-3-yl pyridine derivatives using 3-cyanoacetyl indole. J. Comb. Chem. 2010, 12, 161–167.
  • Zhu, S.; Ji, S.; Su, X.; Sun, C.; Liu, Y. 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.
  • Kathrotiya, H. G.; Patel, M. P. An efficient synthesis of 3′-indolyl substituted pyrido[1,2-a]benzimidazoles as potential antimicrobial and antioxidant agents. J. Chem. Sci. 2013, 125, 993–1001.
  • Zhu, S.; Ji, S.; Zhao, K.; Liu, Y. Multicomponent reactions for the synthesis of new 3′-indolyl substituted heterocycles under microwave irradiation. Tetrahedron Lett. 2008, 49, 2578–2582.
  • Demange, L.; Boeglin, D.; Moulin, A.; Mousseaux, D.; Ryan, J.; Berge, G.; Gagne, D.; Heitz, A.; Perrissoud, D.; Locatelli, V.; Torsello, A.; Galleyrand, J.; Fehrentz, J.; Martinez, J. Synthesis and pharmacological in vitro and in vivo evaluations of novel triazole derivatives as ligands of the ghrelin receptor, 1. J. Med. Chem. 2007, 50, 1939–1957.
  • Franco, L. H.; Joffè, E. B. K.; Puricelly, L.; Tatian, M.; Seldes, A. M.; Palermo, J. A. Indole alkaloids from the tunicate Aplidium meridianum. J. Nat. Prod. 1998, 61, 1130–1132.
  • 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.
  • 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.
  • Kawasaki, I.; Yamashita, M.; Ohta, S. Total synthesis of nortopsentins A-D, marine alkaloids. Chem. Pharm. Bull. 1996, 44, 1831–1839.
  • Higuchi, K.; Takei, R.; Kouko, T.; Kawasaki, T. Total synthesis of marine bisindole alkaloid (+)-cis-dihydrohamacanthin B. Synthesis 2007, 669–674.
  • Gu, X.; Wan, X.; Jiang, B. Syntheses and biological activities of bis(3-indolyl)thiazoles, analogues of marine bis(indole)alkaloid nortopsentins. Bioorg. Med. Chem. Lett. 1999, 9, 569–572.
  • Diana, P.; Carbone, A.; Barraja, P.; Montalbano, L.; Martorana, A.; Dattolo, G.; Gia, O.; Via, L. D.; Cirrincione, G. Synthesis and antitumor properties of 2,5-bis(3′-indolyl)thiophenes: Analogues of marine alkaloid nortopsentin. Bioorg. Med. Chem. Lett. 2007, 17, 2342–2346.
  • Sebahar, P. R.; Williams, R. M. The asymmetric total synthesis of (+)- and (–)-spirotryprostatin B. J. Am. Chem. Soc. 2000, 122, 5666–5667.
  • Kang, T. H.; Matsumoto, K.; Tohda, M.; Murakami, Y.; Takayama, H.; Kitajima, M.; Aimi, N.; Watanabe, H. Pteropodine and isopteropodine positively modulate the function of rat muscarinic M1 and 5-HT2 receptors expressed in Xenopus oocyte. Eur. J. Pharmacol. 2002, 444, 39–45.
  • Palucki, B. L.; Feighner, S. D.; Pong, S. S.; McKee, K. K.; Hrenuik, D. L.; Tan, C.; Howard, A. D.; Van der Ploeg, L. H. Y.; Patchett, A. A.; Nargund, R. P. Spiro(indoline-3,4′-piperidine) growth hormone secretagogues as ghrelin mimetics. Bioorg. Med. Chem. Lett. 2001, 11, 1955–1957.
  • Fadda, A. A.; El-Mekabaty, A.; Mousa, I. A.; Elattar, K. M. Chemistry of 3-(1H-indol-3-yl)-3-oxopropanenitrile. Synth. Commun. 2014, 44, 1579–1599.
  • El-Mekabaty, A.; Etman, H. A.; Mosbah, A. Synthesis of some new fused pyrazole derivatives bearing indole moiety as antioxidant agents. J. Heterocyclic Chem., in press. DOI: 10.1002/jhet.2218.
  • Remers, W. A. Indoles, part I. In Heterocyclic Compounds; W. J. Houlihan (Ed.); Wiley: New York, 1972.
  • Oddo, B. Syntheses in the indole group, I; Alkylindoles. Gazz. Chim. Ital. 1911, 41, 222–234; Chem. Abstr. 1911, 5, 2638.
  • Salway, A. H. XLIII: Researches on the constitution of physostigmine, part II: The synthesis of 3-dimethyl-aminoacetyl-2-methylindole and 2-α-dimethyl-amino-γ-hydroxypropylindole. J. Chem. Soc. 1913, 103, 351–361.
  • Majima, R.; Kotake, M. Synthesis in the indole group II: The influence of the solvent on the Grignard reaction. Ber. Deut. Chem. Ges. 1922, 55B, 3865–3872.
  • Mingoia, Q. Some new indole compounds with mixed function. Gazz. Chim. Ital. 1931, 61, 646–650; Chem. Abstr. 1932, 26, 1279.
  • Sanna, G. Halo ketones of indole, II. Gazz. Chim. Ital. 1929, 59, 838–850; Chem. Abstr. 1930, 24, 2127.
  • Sanna, G. Halogenated ketones of indole, I. Gazz. Chim. Ital. 1929, 59, 169–181; Chem. Abstr. 1929, 23, 4215.
  • Ames, D. E.; Bowman, R. E.; Evans, D. D.; Jones, W. A. The synthesis of some indolylalkylamines. J. Chem. Soc. 1956, 1984–1989.
  • Kalir, A.; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem. 1966, 9, 341–344.
  • Ridley, H. F. The best synthetic methods for indole Grignard reagents. Ph.D. thesis, University of London, May 1966.
  • Ganellin, C. R.; Hollyman, D. R.; Ridley, H. F. Aminoalkylation of metal derivatives of indole, part II: Coupling of indolylmagnesium iodides with halogenoalkylamines. J. Chem. Soc. 1967, 2220–2225.
  • Sanna, G. Polyhalogenated ketones of indole. Gazz. Chim. Ital. 1931, 61, 60–74; Chem. Abstr. 1931, 25, 2720.
  • Sanna, G. Polyhalogenated ketones, II: Indole. Rend. Seminario Facolta Sci. Univ. Cagliari 1934, 4, 28–33; Chem. Abstr. 1936, 30, 6363.
  • Sanna, G.; Athene, F. Polyhalogenated ketones, IVa: Skatole. Rend. Seminario Facolta Sci. Univ. Cagliari 1934, 4, 62–66; Chem. Abstr. 1936, 30, 6364.
  • Cardillo, B.; Casnati, G.; Pochini, A.; Ricca, A. Alkylation of indole sodium salt as ambifunctional nucleophilic system. Tetrahedron l967, 23, 3771–3783.
  • Bergman, J.; Venemalm, L. Acylation of the zinc salt of indole. Tetrahedron 1990, 46, 6061–6066.
  • Anthony, W. C. Novel synthesis of heterocyclic ketones. J. Org. Chem. 1960, 25, 2049–2053.
  • Preobrazhenskaya, M. N.; Orlova, L. M.; Liberman, S. S.; Mosina, G. S.; Avramenko, V. G.; Sorokina, N. P.; Suvorov, N. N. Synthesis and study of the pharmacological activity of hydroxyketones in the indole series. Pharm. Chem. J. 1972, 6, 33–38.
  • Degraw, J. I.; Kennedy, J. G.; Skinner, W. A. The preparation and reduction of 5-cyano-3-indolylketones: Synthesis of 5-cyanotryptamines. J. Heterocycl. Chem. 1966, 3, 9–13.
  • Murakami, Y.; Tani, M.; Suzuki, M.; Sudoh, K.; Uesato, M.; Tanaka, K.; Yokoyama, Y. Synthetic studies on indoles and related compounds, XII: A simple general method for the C-3 acylation of ethyl indole-2-carboxylates. Chem. Pharm. Bull. 1985, 33, 4707–4716.
  • Bergman, J. The reaction of N-acylpyridinium salts with indole. J. Heterocycl. Chem. 1970, 7, 1071–1076.
  • Bergman, J.; Backvall, J. E.; Lindstrom, J. O. Synthesis and reactions of some 3-(2-haloacyl)indoles. Tetrahedron 1973, 29, 971–976.
  • Thompson, M. J.; Louth, J. C.; Ferrara, S.; Sorrell, F. G.; Irving, B. J.; Cochrane, E. J.; Meijer, A. J. H. M.; Chen, B. Structure–activity relationship refinement and further assessment of indole-3-glyoxylamides as a lead series against Prion disease. Chem. Med. Chem. 2011, 6, 115–130.
  • Ketcha, D. M.; Gribble, G. W. A convenient synthesis of 3-acylindoles via Friedel–Crafts acylation of 1-(pheny1sulfonyl)indole: A new route to pyridocarbazole-5,11-quinones and ellipticine. J. Org. Chem. 1985, 50, 5451–5457.
  • Watanabe, T.; Kobayashi, A.; Nishiura, M.; Takahashi, H.; Usui, T.; Kamiyama, I.; Mochizukin, N.; Noritake, K.; Yokoama, Y.; Murakami, Y. Synthetic studies on indoles and related compounds, XXVI: The debenzylation of protected indole nitrogen with aluminum chloride. Chem. Pharm. Bull. 1991, 39, 1152–1156.
  • Ottoni, O.; Neder, A. D. 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.
  • Abdel-Motaleb, R. M.; Makhloof, A. M. A. S.; 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.
  • Mutschler, E.; Winkler, W. Synthesis of 1-, 2- and 3-(aminoacetyl)indoles and 1-(aminoacetyl)indolines. Arch. Pharm. (Weinheim) 1978, 311, 248–255.
  • Bergman, J.; Carlsson, R.; Misztal, S. The reaction of some indoles and indolines with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Acta Chem. Scand. 1976, B30, 853–862.
  • Hasimbegovic, V.; Slätt, J.; Bergman, J.; Janosik, T. The synthesis of some 3-acylindoles revisited. J. Heterocycl. Chem. 2007, 44, 1213–1217.
  • Fujii, T.; Yoshifuji, S.; Ito, H. Quinolizidines, XXV: An extension of the “lactim ether route” to the racemic syntheses of several indolo[2,3-a] quinolizidine alkaloids. Chem. Pharm. Bull. 1988, 36, 3348–3353.
  • Ohba, M.; Ohashi, T.; Fujii, T. Quinolizidines, XXIX: Preparation of (–)-dihydrocorynantheol. Heterocycles 1991, 32, 319–328.
  • Santanay, C.; Blasko, G.; Honty, K.; Dornyei, G. Yohimbine and reserpine families. In The Alkaloids, Vol. 27; Academic Press: Orlando, 1986; pp. 131–268.
  • Timmermans, P. B. M. W. M.; Van Zweiten, P. A. α2-Adrenoceptors: Classification, localization, mechanisms, and targets for drugs. J. Med. Chem. 1982, 25, 1389–1401.
  • Aube, J. An enantioselective synthesis of (–)-alloyohimbane. Tetrahedron Lett. 1988, 29, 4509–4512.
  • Fujii, T.; Yoshifuji, S.; Ito, H. A new synthetic route to indoliquinolizidine alkaloids. Heterocycles 1977, 7, 149–154.
  • Gitto, R.; De Luca, L.; Ferro, S.; Occhiuto, F.; Samperi, S.; De Sarro, G.; Russo, E.; Ciranna, L.; Costa, L.; Chimirri, A. Computational studies to discover a new NR2B/NMDA receptor antagonist and evaluation of pharmacological profile. Chem. Med. Chem. 2008, 3, 1539–1548.
  • Gitto, R.; Luca, L. D.; Ferro, S.; Citraro, R.; Sarro, G. D.; Costa, L.; Ciranna, L.; Chimirri, A. Development of 3-substituted-1H-indole derivatives as NR2B/NMDA receptor antagonists. Bioorg. Med. Chem. 2009, 17, 1640–1647.
  • Fujii, T.; Ohba, M.; Sasaki, N. Quinolizidines, IX: An improved procedure for the synthesis of indolo[2,3-a]quinolizidine from 3-(2-piperidinoethyl) indole. Heterocycles 1984, 22, 1805–1810.
  • Aube, J.; Wang, Y.; Hammond, M.; Tanol, M.; Takusagawa, F.; Velde, D. V. Synthetic aspects of an asymmetric nitrogen insertion process: Preparation of chiral, non-racemic caprolactams and valerolactams: Total synthesis of (–)-alloyohimbane. J. Am. Chem. Soc. 1990, 112, 4879–4891.
  • Povalyaeva, O. S.; Kurkovskaya, L. N.; Vigdorchik, M. M.; Suvorov, N. N. Synthesis of thiazolidinyl derivatives of indoles from 2-chloro-1-(3-indolyl)ethanones. Zh. Org. Khim. 1987, 23, 1294–1304.
  • Tsujii, S.; Rinehart, K. L.; Gunasekera, S. P.; Kashman, Y.; Cross, S. S.; Lui, M. S.; Pomponi, S. A.; Diaz, M. C. Topsentin, bromotopsentin, and dihydrodeoxybromotopsentin: Antiviral and antitumor bis(indoly1)imidazoles from Caribbean deep-sea sponges of the family Halichondriidae: Structural and synthetic studies. J. Org. Chem. 1988, 53, 5446–5453.
  • Goff, D.; Fernandez, J. The preparation of 2,4-disubstituted thiazoles on solid support. Tetrahedron Lett. 1999, 40, 423–426.
  • Mathvink, R. J.; Tolman, J. S.; Chitty, D.; Candelore, M. R.; Cascieri, M. A.; Colwell, L. F.; Deng, J. L.; Feeney, W. P.; Forrest, M. J.; Hom, G. J.; MacIntyre, D. E.; Tota, L.; Wyvratt, M. J.; Fisher, M. H.; Weber, A. E. Potent, selective 3-pyridylethanolamine β3 adrenergic receptor agonists possessing a thiazole benzenesulfonamide pharmacophore. Bioorg. Med. Chem. Lett. 2000, 10, 1971–1973.
  • Chihiro, M.; Nagamoto, H.; Takemura, I.; Kitano, K.; Komatsu, H.; Sekiguchi, K.; Tabusa, F.; Mori, T.; Tominaga, M.; Yabuuchi, Y. Novel thiazole derivatives as inhibitors of superoxide production by human neutrophils: Synthesis and structure–activity relationships. J. Med. Chem. 1995, 38, 353–358.
  • Jiang, B.; Gu, X. H. Syntheses and cytotoxicity evaluation of bis(indolyl)thiazole, bis(indolyl)pyrazinone, and bis(indolyl)pyrazine: Analogues of cytotoxic marine bis(indole) alkaloid. Bioorg. Med. Chem. 2000, 8, 363–371.
  • Nagel, A. A.; Rosen, T.; Rizzi, J.; Daffeh, J.; Guarino, K.; Nowakowski, J.; Vincent, L. A.; Heym, J.; Mclean, S.; Seeger, T.; Connolly, M.; Schmidt, A. W.; Siok, C. Aromatic thiazole derivatives: Structurally novel and selective serotonin-3 receptor antagonists. J. Med. Chem. 1990, 33, 13–16.
  • Zawistoski, M. P. Synthesis of 4-[3-(1H)-indolyl]-2-[N-guanidinomethyl] thiazole dihydrochloride. J. Heterocycl. Chem. 1990, 27, 519–521.
  • LaMattina, J. L.; McCarthy, P. A.; Reiter, L. A.; Holt, W. F.; Yeh, L. Antiulcer agents: 4-Substituted 2-guanidinothiazoles: Reversible, competitive, and selective inhibitors of gastric H+, K+-ATPase. J. Med. Chem. 1990, 33, 543–552.
  • Smushkevich, Y. I.; Babueva, T. M.; Suvorov, N. N. Indole derivatives, XXXIV: Synthesis of 2-substituted 4-(3\-indolyl)thiazoles. Chem. Heterocycl. Compd. 1969, 5, 73–74.
  • Somei, M.; Yamada, Y.; Kitagawa, K.; Sugaya, K.; Tomita, Y.; Yamada, F.; Nakagawa, K. Synthetic study directed toward novel multi-linked heterocycles. Heterocycles 1997, 45, 435–438.
  • Bansal, E.; Srivastava, V. K.; Kumar, A. Synthesis of some new formazanyl-thiazolyl-indoles and formazanyl-oxazolyl-indoles as inflammation inhibitors. Indian J. Chem. 2000, 39B, 357–362.
  • Thomas, K. K.; Reshmy, R.; Ushadevi, K. S. Synthesis of a few novel bioactive 2-substituted amino-5-indol-3-oyl-4-phenylthiazoles. J. Indian Chem. Soc. 2007, 84, 1016–1019.
  • Thomas, K. K.; Reshmy, R. Synthesis and characterization of novel azacyclo-bound thiazoles having heteroyl attachments. Acta Cien. Ind., Chem. 2007, 33, 523–528.
  • Abbs Fen Reji, T. F.; Rajasekharan, K. N. Synthesis of 3-(2,4-diamino-5-thiazolyl)carbonyl indoles. J. Saudi Chem. Soc. 2008, 12, 269–274.
  • Johnsona, A. L.; Bergman, J. Synthetic approaches towards an indole alkaloid isolated from the marine sponge Halichondria melanodocia. Tetrahedron 2006, 62, 10815–10820.
  • Moody, C. J.; Ward, J. G. [2,3] Fused indoles, part 2: Synthesis of 1,8-dihydropyrrolo[2,3-b]indoles and photochemical rearrangement of their 1-allyl derivatives. J. Chem. Soc. Perkin Trans. 1 1984, 2903–2909.
  • Roy, S.; Haque, S.; Gribble, G. W. Synthesis of novel oxazolyl-indoles. Synthesis 2006, 23, 3948–3954.
  • Nakajima, M.; Loeschorn, C. A.; Cimbrelo, W. E.; Anselme, J. P. Substituted pyrazines from the catalytic reduction of α-azidoketones. Org. Pre. Proc. Int. 1980, 12, 265–268.
  • Deng, W. P.; Nam, G.; Fan, J.; Kirk, K. L. Syntheses of β,β-difluorotryptamines. J. Org. Chem. 2003, 68, 2798–2802.
  • Hellberg, J.; Moge, M. Synthesis of some bis(aryl)substituted tetrathiafulvalenes. Synth. Metals 1993, 55–57, 2124–2127.
  • Smushkevich, Y. I.; Zhigachev, V. E.; Sulima, A. V.; Suvorov, N. N. Indole derivatives, LIII: α-Oxo epoxides of the indole series. Chem. Heterocycl. Compd. 1970, 6, 1004–1006.
  • Braekman, J. C.; Daloze, D.; Stoller, C. Synthesis of topsentin-A, a bisindole alkaloid of the marine sponge Topsentia genitrix. Bull. Soc. Chim. Belg. 1987, 96, 809–812; Chem. Abstr. 1989, 109, 73723.
  • Sozinov, V. N.; Orlova, L. M.; Mashkovskii, M. D.; Suvorov, N. N. Investigation of the psychotropic activity of 3-tert-butylaminoacylindoles. Pharm. Chem. J. 1981, 15, 412–415.
  • Povalyaeva, O. S.; Rodionov, V. Ya.; Suvorov, N. N. Synthesis of indole-thiazolidines based on 2-chloro-1-(indol-3-yl)ethanone and its substituted derivatives, III: Reaction of 2-chloro-1-(indol-3-yl)ethanone and its derivatives with aminoethyl derivatives of thiophosphoric acid. Zh. Org. Khim. 1991, 27, 2217–2223.
  • Povalyaeva, O. S.; Rodionov, V. Ya.; Suvorov, N. N. Synthesis of indole thiazolidines based on 2-chloro-1-(indol-3-yl)ethanone and its substituted derivatives, II: Reaction of 2-chloro-1-(indol-3-yl)ethanone and its derivatives with various cystamine derivatives. Zh. Org. Khim. 1991, 27, 2210–2216.
  • Baron, M.; Cointet, P. d.; Bauduin, G.; Pietrasanta, Y.; Pucci, B. Synthesis of water-soluble 4-(3-indolyl)-2,5-dihydro-2-furanones. Bull. Soc. Chim. Fr. 1982, 2, 249–256.
  • Ma, L. J.; Inokuchi, T. Solvent-free microwave-assisted multi-component reaction for preparation of 2-amino-1-aryl-2-(cyclohex-1-enyl)ethanones as precursors of pseudoephedrine analogues. Chem. Commun. 2010, 46, 7037–7039.
  • Bergman, J.; Backvall, J. E. Base-induced reactions of 3-(α-haloacyl)indoles. Tetrahedron Lett. 1973, 31, 2899–2902.
  • Bergman, J.; Backvall, J. E. Base-induced rearrangements of 3-(α-haloacyl)indoles: A convenient route to indole-3-acetic acids and tryptopholes. Tetrahedron 1975, 31, 2063–2073.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.