Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 9
1,059
Views
38
CrossRef citations to date
0
Altmetric
SYNTHETIC COMMUNICATIONS REVIEWS

Reactivity of indolizines in organic synthesis

, &
Pages 719-744 | Received 06 Nov 2015, Published online: 04 May 2016

References

  • Kloubert, T.; Kretschmer, R.; Görls, H.; Westerhausen, M. [1-Methoxy-3-(pyridin-2-yl)indolizin-2-yl](pyridin-2-yl)methanone. Acta Crystallogr Sect E Struct Rep 2012, 68(9), o2631–o2632.
  • Michael, J. P. Indolizidine and quinolizidine alkaloids. Nat. Prod. Rep. 1997, 14, 21–41.
  • Takahata, H.; Momose, T. In The Alkaloids; G. A. Cordell (Ed.); Academic Press: San Diego, CA, 1993; Vol. 44, Chapter 3.
  • Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry: Stereoselective Synthesis; Atta-ur-Rahman (Ed.); Elsevier: New York, 1995; vol. 16, part J, 453–502.
  • Okano, T.; Sakaida, T.; Eguchi, S. Synthesis of indolizidine derivatives trifluoromethylated at bridgehead position via acyl iminium ion intermediates derived from ring-chain tautomerism of 5,5,5-trifluoro-4-oxopentanoyl arylethylamides. Heterocycles 1997, 44, 227–236.
  • Comins, D. L.; Zhang, Y.-M. Anionic cyclizations of chiral 2,3-dihydro-4-pyridones: A five-step, asymmetric synthesis of indolizidine 209D. J. Am. Chem. Soc. 1996, 118, 12248–12249.
  • Michael, J. P.; Gravestock, D. Synthesis of (±)-indolizidine 209B and a new 209B diastereoisomer. Synlett 1996, 10, 981–982.
  • Thanh, G. V.; Célérier, J.-P.; Lhommet, G. Enantioselective synthesis of (–)-indolizidine 239AB [(3 R,5S,8aR)-3-butyl-5-(3-hydroxypropyl)-octahydro-indolizine]. Tetrahedron: Asymmetry 1996, 7, 2211–2212.
  • Chan, C.; Cocker J. D.; Davies, H. G.; Gore, A.; Green, R. H. Indolizidine derivatives as potential substance P antagonists. Bioorg. Med. Chem. Lett. 1996, 6, 161–164.
  • Li, Y.; Marks, T. J. Coupled organolanthanide-catalyzed C−N/C-C bond formation processes: Efficient regiospecific assembly of pyrrolizidine and indolizidine skeletons in a single catalytic reaction. J. Am. Chem. Soc. 1996, 118, 707–708.
  • Takahata, H.; Bandoh, H.; Momose, T. An asymmetric synthesis of the ant venom alkaloid (3s,5s,8ar)-3-butyl-5-(4-pentenyl)indolizidine via the Sharpless asymmetric dihydroxylation. Heterocycles 1996, 42, 39–42.
  • Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. Tandem Beckmann and Huisgen–White rearrangement of the 9-azabicyclo[3.3.1]nonan-3-one system, part 2.1: The second mode of the rearrangement leading to 6-(prop-1-enyl)piperidin-2-ylacetic acid, a versatile intermediate for the syntheses of piperidine alkaloids (+)-pinidine and (+)-monomorine I. J. Chem. Soc. Perkin Trans. 1 1997, 113–120.
  • Lee, E.; Kang, T. S.; Chung, C. K. Radical cyclization of β-aminoacrylates: Expedient synthesis of (+)-monomorine 1 and (+)-indolizidine 195B. Bull. Korean Chem. Soc. 1996, 17, 212–214.
  • Solladié, G.; Chu, G.-H. Total synthesis of (+)-indolizidine 195 B and (+)-monomorine. Tetrahedron Lett. 1996, 37, 111–114.
  • Munchhof, M. J.; Meyers, A. I. A novel asymmetric route to chiral, nonracemic cis-2,6-disubstituted piperidines: Synthesis of (+)-pinidinone and (+)-monomorine. J. Am. Chem. Soc. 1995, 117, 5399–5400.
  • Borrows, E. T.; Holland, D. O. The chemistry of the pyrrocolines and the octahydropyrrocolines. Chem. Rev. 1948, 42, 611.
  • Singh, G. S.; Mmatli, E. E. Recent progress in synthesis and bioactivity studies of indolizines. Eur. J. Med. Chem. 2011, 46, 5237–5257.
  • Hosaan, A.; Fadda, A. A. Enamine rearrangement of pyridinium salts to indole ring: A combined experimental and molecular modeling study. J. Heterocycl. Chem. 2013, 50, 638–644.
  • Elattar, K. M.; Abozeid, M. A.; Mousa, I. A.; El-Mekabaty, A. Advances in 1,2,4-triazepines chemistry. RSC Adv. 2015, 5, 106710–106753. doi:10.1039/C5RA21108E.
  • Elattar, K. M.; Abozeid, M. A.; Etman, H. A. Developments in 1,2,5-triazepines chemistry: Reactions and synthetic applications. Synth. Commun. 2016, 46(2), 93–117. doi:10.1080/00397911.2015.1109126
  • Fadda, A. A.; Abdel-Galil, E.; Elattar, K. M. Chemistry of 3-oxo-N-(pyridin-2-yl)butanamide and related compounds. Synth. Commun. 2015, 45(18), 2053–2082.
  • Fadda, A. A.; Elattar, K. M. Reactivity of dehydroacetic acid in organic synthesis. Synth. Commun. 2016, 46(1), 1–30. doi:10.1080/00397911.2015.1092549
  • Fadda, A. A.; El-Hadidy, S. A.; Elattar, K. M. Advances in 1,8-naphthyridines chemistry. Synth. Commun. 2015, 45(24), 2765–2801.
  • Fadda, A. A.; Bayoumy, N. M.; Elattar, K. M. Recent progress in the chemistry of 2-tosylacetonitrile. Synth. Commun. 2015, 45(23), 2637–2675.
  • Fadda, A. A.; Elattar, K. M. Utility of enaminonitriles in heterocyclic synthesis: Synthesis of some new azepine, azocine and pyrroldione derivatives. J. Heterocycl. Chem. 2014, 51(6), 1697–1704.
  • 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(11), 1579–1599.
  • Fadda, A. A.; El-Mekabaty, A.; Elattar, K. M. Chemistry of enaminonitriles of pyrano[2,3-c]pyrazole and related compounds. Synth. Commun. 2013, 43(20), 2685–2719.
  • Gouda, M. A.; Berghot, M. A.; Abd El-Ghani, G. E.; Elattar, K. M.; Khalil, A. M. Utility of 2-aminothiophene-3-carboxamides in heterocyclic synthesis. Turk. J. Chem. 2011, 35, 815–837.
  • Hickman, J. A.; Wibberley, D. G. Indolizines, part V: The synthesis of 3-amino- and 3-acetamido-indolizines and their precursors, the 3-azo-, -nitroso-, -nitro-, and -acetyl-indolizines. J. Chem. Soc., Perkin Trans. 1 1972, 2954–2958.
  • Borrows, E. T.; Holland, D. O.; Kenyon, J. The chemistry of the pyrrocolines, part II: Nitroso-derivatives of some substituted pyrrocolines. J. Chem. Soc. 1946, 1075–1077.
  • Borrows, E. T.; Holland, D. O.; Kenyon, J. The chemistry of the pyrrocolines, part III: Nitration. J. Chem. Soc. 1946, 1077–1083.
  • Greci, L.; Ridd, J. H. The kinetics of nitration and nitrosation of 1-methyl-2-phenylindolizine. J. Chem. Soc., Perkin Trans. 2 1979, 312–316.
  • Lins, C. L. K.; Block, J. H.; Doerge, R. F. Nitro- para- and meta- substituted 2-phenylindolizines as potential antimicrobial agents. J. Pharm. Sci. 1982, 71(5), 556–561.
  • Holliman, F. G.; Schickerling, H. A. Cyanine dyes containing the pyrrocoline nucleus, part I. J. Chem. Soc. 1951, 914–920.
  • Buu-Hoï, N. P.; Binh, L. C.; Loc, T. B.; Xuong, N. D.; Jacquignon, P. Carcinogenic nitrogen compounds, part XXII: cyclo-Hexyl derivatives of benzacridines, carbazole, and other nitrogen heterocycles. J. Chem. Soc. 1957, 3126–3129.
  • Scholtz, M. Über die Natur des Picolids und Pyrrocolins. Chem. Ber. 1912, 45(2), 1718–1725.
  • Rossiter, E. D.; Saxton, J. E. Studies in the pyrrocoline series. J. Chem. Soc. 1953, 8, 3654–3659.
  • Fuentes, O.; Paudler, W. W. Some formylation reactions of imidazo[1,5-a] pyridine and pyrrocoline. J. Heterocycl. Chem. 1975, 12(2), 379–383.
  • Holland, D. O.; Nayler, J. H. C. The chemistry of the pyrrocolines, part VII: Further experiments with 2-methylpyrrocoline. J. Chem. Soc. 1955, 1504–1512.
  • Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Palladium-catalyzed arylation and heteroarylation of indolizines. Org. Lett. 2004, 6(7), 1159–1162.
  • Nasielski, J.; Siberdt, F.; De Bue, G. Unexpected dimers in the synthesis of 2-styrylindolizine. Bull. Soc. Chim. Belges 1997, 106(2), 97–108.
  • Yamashita, Y.; Suzuki, D.; Masumura, M. Synthesis of vinyl-substituted indolizine derivatives by a novel reaction of indolizines with ethoxyethylenes having electron-withdrawing substituents. Heterocycles 1981, 16(9), 1499–1502.
  • Kuznetsov, A. G.; Bush, A. A.; Rybakov, V. B.; Babaev, E. V. An improved synthesis of some 5-substituted indolizines using regiospecific lithiation. Molecules 2005, 10(9), 1074–1083.
  • Robinson, R.; Saxton, J. E. Experiments on the synthesis of the ring systems of strychnine and allied alkaloids, part II. J. Chem. Soc. 1952, 976–982.
  • Rossiter, E. D.; Saxton, J. E. Studies in the pyrrocoline series. J. Chem. Soc. 1953, 3654–3660.
  • Armarego, W. L. F. Ionization and ultraviolet spectra of indolizines. J. Chem. Soc. 1964, 4226–4234.
  • Walter, L. A.; Margolis, P. 2-Phenylindolizines. J. Med. Chem. 1967, 10(3), 498–499.
  • Davies, G. M.; Downham, R.; Edwards, P.; Payne, L. J.; Sibley, G. E. M. 2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamide derivatives and related compounds as antifungal agents. Eur. Patent, EP 2173749 B1, 2011.
  • Khorkhe, R. A.; Soldatova, S. A.; Soldatenkov, A. T.; Ryashentseva, M. A.; Prostakov, N. S. Hydrogenation of compounds containing an indolizine moiety and of 1-benzylisoquinoline over rhenium heptasulfide. Bull. Acad. Sci. USSR, Divis. Chem. Sci. 1991, 40(6), 1253–1256; Izvestiya Akad. Nauk SSSR, Seriya Khim. 1991, 6, 1413–1416.
  • Dieter, R. K.; Chen, N.; Watson, R. T. Copper-mediated scalemic organolithium reagents in alkaloid syntheses. Tetrahedron 2005, 61(13), 3221–3230.
  • Miyano, S.; Fujii, S.; Yamashita, O.; Toraishi, N.; Sumoto, K. Synthesis of Δ1[9]- and/or Δ8[9]-dehydroindolizidines and related compounds. J. Heterocycl. Chem. 1982, 19(6), 1465–1468.
  • De Wang, M.; Alper, H. Catalytic and photolytic reactions of 5,6,7,8-tetrahydroindolizines with oxygen. Tetrahedron Lett. 1995, 36(38), 6855–6858.
  • Pandey, G.; Reddy, G. D.; Chakrabarti, D. Stereoselectivity in the photoinduced electron transfer (PET)–promoted intramolecular cyclisations of 1-alkenyl-2-silyl-piperidines and -pyrrolidines: Rapid construction of 1-azabicyclo[m.n.0]alkanes and stereoselective synthesis of (±)-isoretronecanol and (±)-epilupinine. J. Chem. Soc., Perkin Trans. 1, 1996, 219–224.
  • Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. The synthesis and biological activity of (±)-(1α, 2α,8α)-indolizidine-1,2-diol. Aust. J. Chem. 1984, 37(7), 1503–1509.
  • Kuznetsov, A. G.; Bush, A. A.; Babaev, E. V. Synthesis and reactivity of 5-Br(I)-indolizines and their parallel cross-coupling reactions. Tetrahedron 2008, 64(4), 749–756.
  • Sawada, K.; Okada, S.; Kuroda, A.; Watanabe, S.; Sawada, Y.; Tanaka, H. 4-(Benzoylindolizinyl)butyric acids: Novel nonsteroidal inhibitors of steroid 5a-reductase, III. Chem. Pharm. Bull. 2001, 49(7), 799–813.
  • Østby, O. B.; Dalhus, B.; Gundersen, L.-L.; Rise, F.; Bast, A.; Haenen, G. R. M. M. Synthesis of 1-substituted 7-cyano-2,3-diphenylindolizines and evaluation of antioxidant properties. Eur. J. Org. Chem. 2000, 22, 3763–3770.
  • For recent reviews, see (a) Michael, J. P. Simple indolizidine and quinolizidine alkaloids. Alkaloids Chem. Biol. 2001, 55, 91–258; (b) Michael, J. P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 2002, 19(6), 742–760.
  • Halab, L.; Becker, J. A. J.; Darula, Z.; Tourwe, D.; Kieffer, B. L.; Simonin, F.; Lubell, W. D. Probing opioid receptor interactions with azacycloalkane amino acids: Synthesis of a potent and selective ORL1 antagonist. J. Med. Chem. 2002, 45(24), 5353–5357.
  • Pearson, W. H.; Hembre, E. J. Synthesis of novel glycosidase-inhibitory hydroxymethyl-substituted polyhydroxylated indolizidines: Ring-expanded analogs of the pyrrolizidine alkaloids alexine and australine. J. Org. Chem. 1996, 61(16), 5546–5556.
  • Windgassen Jr., R. J.; Saunders Jr., W. H.; Boekelheide, V. Cyclazines: A new class of aromatic heterocycles. J. Am. Chem. Soc. 1959, 81(6), 1459–1465.
  • Renard, M.; Gubin, J. Metallation of 2-phenylindolizine. Tetrahedron Lett. 1992, 33(31), 4433–4434.
  • Hideo, K.; Eiichi, K.; Nobuo, O.; Kagari, Y.; Kazuya, M.; Shinji, K.; Miyoji, H. Studies on antispasmodics, V: Synthesis and anticholinergic activity of n-alkyl 1- and 2-diarylmethylene-indolizidinium bromides. Chem. Pharm. Bull. 1980, 28(7), 2194–2206.
  • Kumar, S.; Sahu, D. P. Friedel–Crafts heteroarylation of (hetero)arenes: A facile entry to 4-(hetero)aryl quinazolines and quinolines. J. Heterocycl. Chem. 2009, 46(4), 748–755.
  • Tatarov, A.; Kurbatov, S.; Borodkin, G.; Goumont, R.; Terrier, F. SEAr–SNAr couplings of indolizines and related pyrrole derivatives with superelectrophilic nitrobenzoxadiazoles. Tetrahedron 2010, 66(4), 995–1006.
  • Amaral, M. F. Z. J.; Deliberto, L. A.; De Souza, C. R.; Naal, R. M. Z. G.; Naal, Z.; Clososki, G. C. Synthesis, photophysical, and electrochemical properties of 2,5-diaryl-indolizines. Tetrahedron 2014, 70(20), 3249–3258.
  • Mirek, J.; Haas, A. The reaction of indolizines and acetylindolizines with trifluoromethylsulfenyl chloride. J. Fluorine Chem. 1981, 19(1), 67–70.
  • Brase, S.; de Meijere, A. In Handbook of organopalladium chemistry for organic synthesis, E. Negishi (Ed.); John Wiley and Sons: New York, 2002; Vol. 1, pp. 1369–1404.
  • Brase, S.; de Meijere, A. In Handbook of organopalladium chemistry for organic synthesis; E. Negishi (Ed.); John Wiley and Sons: New York, 2002; Vol. 1, pp. 1405–1430.
  • Seregin, I. V.; Ryabova, V.; Gevorgyan, V. Direct palladium-catalyzed alkynylation of N-fused heterocycles. J. Am. Chem. Soc. 2007, 129, 7742–7743.
  • Concellón, J. M.; Suárez, J. R.; García-Granda, S.; Díaz, M. R. Synthesis and stereoselective lithiation of enantiopure 2-(1-aminoalkyl)aziridine–borane complexes. Angew. Chem., Int. Ed. Engl. 2004, 43, 4333–4336.
  • BF3 complexes of amines are less amenable to isolation and direct characterization as compared to BH3 complexes.
  • Kessar, S. V.; Singh, P.; Singh, K. N.; Venugopalan, P.; Kaur, A.; Bharatam, P. V.; Sharma, A. K. An experimental and computational study of stereoselectivity and reactivity in Lewis acid–promoted lithiation–substitution of tertiary amines. J. Am. Chem. Soc. 2007, 129, 4506–4507.
  • Gubin, J.; Rosseels, G. Indolizine derivatives, pharmaceutical compositions and methods containing same. Labaz, US 4103012 A, 1978.
  • Šafář, P.; Žúžiová, J.; Marchalín, S.; Prónayová, N.; Švorc, L.; Vrábel, V.; Šesták, S.; Rendić, D.; Tognetti, V.; Joubert, L.; Daïch, A. Combined chemical, biological, and theoretical DFT-QTAIM study of potent glycosidase inhibitors based on quaternary indolizinium salts. Eur. J. Org. Chem. 2012, 28, 5498–5514.
  • Smith, J. O.; Mandal, B. K. A convenient synthesis of 8-substituted indolizines as precursors to 5-substituted cycl{3.2.2}azine derivatives. J. Heterocycl. Chem. 1997, 34, 1441–1446.
  • Bermudez, J.; Fake, C. S.; Joiner, G. F.; Joiner, K. A.; King, F. D.; Miner, W. D.; Sanger, G. J. 5-Hydroxytryptamine (5-HT3) receptor antagonists, 1: Indazole and indolizine-3-carboxylic acid derivatives. J. Med. Chem. 1990, 33(7), 1924–1929.
  • Poty, C.; Gibon, V.; Evrard, G.; Norberg, B.; Vercauteren, D. P.; Gubin, J.; Chatelain, P.; Durant, F. 1-[[4-(Aminoalkoxy)phenyl]sulfonyl]indolizines: A novel class of calcium entry blockers: Relationships between chemical structure, stereoelectronic properties, and anticalcic activity. Eur. J. Med. Chem. 1994, 29(12), 911–923.
  • Oe, T.; Moriwaki, M.; Goto, K.; Hisadome, M. (Yoshitomi Pharmaceutical Industries, Ltd.). Heterocyclic-substituted oxoalkanoic acid derivatives. US Patent 4386092 A, 1983.
  • Jones, G.; Stanyer, J. Synthesis of some hydroxymethyl- and aminomethyl-indolizines. J. Chem. Soc. C 1969, 901–905. doi:10.1039/J39690000901
  • Ghinet, A.; Abuhaie, C.-M.; Gautret, P.; Rigo, B.; Dubois, J.; Farce, A.; Belei, D.; Bîcu, E. Studies on indolizines: Evaluation of their biological properties as microtubule-interacting agents and as melanoma-targeting compounds. Eur. J. Med. Chem. 2015, 89, 115–127.
  • Matviiuk, T.; Mori, G.; Lherbet, C.; Rodriguez, F.; Pasca, M. R.; Gorichko, M.; Guidetti, B.; Voitenko, Z.; Baltas, M. Synthesis of 3-heteryl substituted pyrrolidine-2,5-diones via catalytic Michael reaction and evaluation of their inhibitory activity against InhA and Mycobacterium tuberculosis. Eur. J. Med. Chem. 2014, 71, 46–52.
  • Siberdt F.; Nasielski, J. Indolizines, 2: The reaction of 2-beta-styrylindolizine with dienophiles. Bull. Soc. Chim. Belges 1997, 106(1), 29–38.
  • Batroff, V.; Flitsch, W. Ein neuer Zugang zu [2.3.4]Cyclazinen. Liebigs Ann. Chem. 1987, 621–628.
  • Babu, Y. H.; Kumar, M. A.; Srinivasulu, K.; Reddy, C. S.; Raju, C. N. Synthesis and antimicrobial activity of novel 2-(heteryl-carboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo[3,4-c][1,3,2]diazaphosphole-2-oxides. Arkivoc 2006, 2006(15), 189–197.
  • Masumura, M.; Yamashita, Y. Addition reactions of indolizine derivatives with diethyl azodicarboxylate. Heterocycles 1979, 12(6), 787–790.
  • Flitsch, W.; Heinrich, J. 1,2-Dialkoxycarbonylhydrazine derivatives of pyrroles and indolizines: A new synthesis of cycl[3.2.2]azines. Tetrahedron Lett. 1980, 21(38), 3673–3676.
  • Beverina, L.; Crippa, M.; Landenna, M.; Ruffo, R.; Salice, P.; Silvestri, F.; Versari, S.; Villa, A.; Ciaffoni, L.; Collini, E.; Ferrante, C.; Bradamante, S.; Mari, C. M.; Bozio, R.; Pagani, G. A. Assessment of water-soluble π-extended squaraines as one- and two-photon singlet oxygen photosensitizers: Design, synthesis, and characterization. J. Am. Chem. Soc. 2008, 130(6), 1894–1902.
  • Anisimova, V. A.; Avdyunina, N. I.; Pozharskii, A. F.; Simonov, A. M.; Talanova, L. N. Chloral as a formylating agent for some bridge heterosystems. Chem. Heterocycl. Comp. 1980, 16(4), 409–417; Khim. Geterotsiklicheskikh Soedin. 1980, 16(4), 528–537.
  • Colombo, F.; Cravotto, G.; Palmisano, G.; Penoni, A.; Sisti, M. Three-component indium-mediated domino allylation of 1H-Indole-3-carbaldehyde with electron-rich (hetero)arenes: Highly efficient access to variously functionalized indolylbutenes. Eur. J. Org. Chem. 2008, (16), 2801–2807.
  • Harrell, W. B.; Doerge, R. F. Mannich bases from 2-phenylindolizines III: 1,3-Bis(dialkyl-aminomethyl)-2-phenylindolizines. J. Pharm. Sci. 1968, 57(11), 1989–1991.
  • Harrell, W. B.; Doerge, R. F. New compounds: Mannich bases from 2-phenylindolizines II: 3-Dialkylaminomethyl derivatives. J. Pharm. Sci. 1967, 56(9), 1200–1202.
  • Dieter, R. K.; Watson, R. Synthesis of (±)-isoretronecanol, (±)-curassanecine, (±)-heliotridane, (±)-tashiromine, and (±)-5-epitashiromine via α-(N-carbamoyl)alkylcuprate chemistry. Tetrahedron Lett. 2002, 43, 7725–7728.
  • Sonnenschein, H.; Kosslick, H.; Tittelbach, F. Dehydrogenation of 3-unsubstituted indolizines on platinum on carbon: A facile synthesis of biindolizines. Synthesis 1998, 1998(11), 1596–1598.
  • Kakehi, A.; Ito, S.; Hamaguchi, A.; Okano, T. Facile dehydrogenative dimerization of indolizine derivatives. Bull. Chem. Soc. Jpn. 1981, 54(9), 2833–2834.
  • Prostakov, N. S.; Soldatenkov, A. T.; Bagdadi, M. V.; Brindkha, O. S.; Kuznetsov, V. I.; Reaction of indolizines with elemental sulfur. Chem. Heterocycl. Comp. 1984, 20(10), 1128–1132; Khim. Geterotsiklicheskikh Soedin. 1984, 20(10), 1371–1375.
  • Nasielski, J.; Siberdt, F.; Bue, G. D. Unexpected dimers in the synthesis of 2-styrylindolizine. Bull. Soc. Chim. Belges 1994, 103(12), 719–724.
  • Kreher, T.; Sonnenschein, H.; Schmidt, L.; Huenig, S. Zur Dimerisierung von Indolizinen an Palladium-Kohle. Liebigs Ann. Chem. 1994, 12, 1173–1176.
  • Brooker, L. G. S.; Sprague, R. H. (Eastman Kodak Co.). Pyrrole methine and tri-methine cyanine backing dyes. US Patent 2268798 A, 1940.
  • Weston, M. H.; Nakajima, K.; Back, T. G. Tandem conjugate additions and 3-aza-Cope rearrangements of tertiary allyl amines and cyclic α-vinylamines with acetylenic sulfones: Applications to simple and iterative ring expansions leading to medium and large-ring nitrogen heterocycles. J. Org. Chem., 2008, 73(12), 4630–4637.
  • Tian, J.-Z.; Zhang, Z.-G.; Yang, X.-L.; Fun, H.-K.; Xu, J.-H. Photooxygenation of indolizines via selective excitation of their charge transfer complexes with molecular oxygen. J. Org. Chem. 2001, 66(24), 8230–8235.
  • Galbraith, A.; Small, T.; Boekelheide, V. Reaction of dimethyl acetylenedicarboxylate with pyrrocoline. J. Org. Chem. 1959, 24(4), 582–582.
  • Kaupp, G.; Ringer, E. The first photocycloadditions of indolizine. Tetrahedron Lett. 1987, 28(49), 6155–6158.
  • Kessar, S. V.; Singh, P.; Singh, K. N.; Venugopalan, P.; Kaur, A.; Bharatam, P. V.; Sharma, A. K. An experimental and computational study of stereoselectivity and reactivity in Lewis acid–promoted lithiation–substitution of tertiary amines. J. Am. Chem. Soc. 2007, 129(15), 4506–4507.

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.