Abstract
This article discusses the anodic synthesis of heterocyclic compounds that have appeared during the last decade. The mechanistic aspects involving intramolecular, intermolecular cyclizations and the homogeneous vs heterogeneous anodic oxidations were considered. This review deals with the recent advances in anodic oxidations in which heterocyclic compounds were synthesized through carbon-heteroatom and heteroatom-heteroatom bond formation.
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Lund H, Baizer MM (1991) Organic electrochemistry, 3rd edn. Marcel Dekker, New York
Torii S (1985) Electroorganic synthesis: oxidations, methods and applications-part 1. Kodansha/Verlag Chemie, Tokyo/Weinhem
Shono T (1984) Electroorganic chemistry as a new tool in organic synthesis. Springer, Berlin Heidelberg New York
Shono T (1991) Electroorganic synthesis. Academic Press, New York
Miller LL, Kariv E, Behling JR (1977) Ann Rep in Med Chem 12: 309
Heinze J (1984) Angew Chem Int Ed 23: 831
Lund H (1970) Adv Heterocyclic Chem 12: 213
Baumgartel H, Retzlav KJ (1984). In: Bard AJ, Lund H (eds) Encyclopedia of electrochemistry of the elements, vol 15. Marcel Dekker, New York
Lund H, Tabakovic I (1984) Adv Heterocyclic Chem 36: 235
Armand J, Pinson J (1983). In: Gupta RR (ed) Physical methods in heterocyclic chemistry, vol 7. Wiley, New York
Dryhurst G (1977) Electrochemistry of biological molecules. Academic Press, New York
Toomey JE (1985) Adv Heterocyclic Chem 37: 167
Lacan M, Tabakovic I (1974) Kem Ind (Zagreb) 23: 225
Lacan M, Tabakovic I (1975) Kem Ind (Zagreb) 24: 227
Tabakovic I (1977) Bull Soc Chim (Belgrade) 42: 761
Simonet J, Le Guillanton G (1986) Bull Soc Chim Fr 221
Andrieux CP, Saveant JM (1974) J Electroanal Chem 53: 165
Ammar F, Andrieoux CP, Saveant JM (1973) J Electroanal Chem 53: 407
Andrieux CP, Saveant JM, Tessier D (1975) J Electroanal Chem 63: 429
Anne A, Hapiot P, Moiroux J, Neta P, Saveant JM (1992) J Am Chem Soc 114: 4694
Amatore CM, Saveant JM, (1978) J Electroanal Chem 86: 227
Fry AJ, Little RD, Leonetti J (1994) J Org Chem 59: 5017
Parker VD (1986) Topics in Organic Electrochemistry (Fry AJ, Britton WE, eds.) Plenum Press, New York, Chapter 2
Aalstad B, Parker VD (1982) Acta Chem Scand B36: 187
Aalstad B, Ronlan A, Parker VD (1982) Acta Chem Scand B36: 199
Aalstad B, Ronlan A, Parker VD (1982) Acta Chem Scand B36: 171
Parker VD (1981) Acta Chem Scand B35: 259
Ahlberg E, Parker VD (1981) Acta Chem Scand 121: 73
Aalstad B, Parker VD (1980) Acta Chem Scand 112: 163
Andrieux CP, Delgado G, Saveant JM, Su KB (1993) J Electroanal Chem 348: 107
Tabakovic I, Trkovnik M, Grujic Z (1979) J Chem Soc Perkin 2: 166
Umemoto K (1985) Bull Chem Soc Jpn 58: 2051
Marques EP, Zhang J, Metcalfe RA, Pietro WJ, Lever ABP (1995) J Electroanal Chem 395: 133
Umemoto K (1989) Bull Chem Soc Jpn 62: 3783
Maender OW, Russell GA (1966) J Org Chem 31: 442
Sanicanin Z, Tabakovic I (1988) Electrochim Acta 33: 1601
Tabakovic I, Crljenak S (1981) Heterocycles 16: 699
Jugelt W, Grubert L (1985) Z Chem 25: 408
Jugelt W, Grubert L (1985) Z Chem 25: 442
Jugelt W, Grubert L (1985) Z Chem 25: 443
Grubert L, Jugelt W (1988) Z Chem 28: 187
Grubert L, Jugelt W, Bress HJ, Strietzel U (1990) Z Chem 30: 286
Grubert L, Jugelt W, Bress HJ, Strietzel U, Dombrowski A (1992) Liebigs Ann Chem 885
Gunic E, Tabakovic I (1985) J Org Chem 53: 5081
Warkentin J (1970) Synthesis 279
Butler RN (1984) Chem Rev 84: 249
Lin EC, VanDeMark R (1982) J Chem Soc Chem Commun 1176
Okimoto M, Chiba T (1990) J Org Chem 55: 1070
Wang Q, Amer A, Mohr S, Ertel E, Jochims JC (1993) Tetrahedron 44: 9973
Wang Q, Amer A, Troll C, Fischer H, Jochims JC (1993) Chem Ber 126: 2519
Shawali AS (1993) Chem Rev 93: 2731
Fukui K (1971) Acc Chem Res 4: 57
Barbay G, Caullet C (1974) Tetrahedron Lett 1717
Hammerich O, Parker VD (1972) J Chem Soc Perkin 1: 1718
Okimoto M, Chiba T (1990) J Org Chem 55: 1070
Chiba T, Okimoto M (1992) J Org Chem 57: 1375
Stankovic S, Agray G, Tabakovic I, Gunic E (1991) Acta Cryst 47: 1210
DeLaHoz A, Pardo C, Sanchez A, Elquero J (1990) J Chem Res 294
Ivanova VKh, Brezylin BI, Kitaev Yu 1977 (Izv Akad Nauk SSSR Ser Khim 2: 393
Grujic Z, Tabakovic I, Trkovnik M (1981) Tetrahedron Lett 22: 4823
Tabakovic I, Grujic Z, Bejtovic Z (1983) J Heterocylic Chem 20: 635
Koch D, Schafer H (1973) Angew Chem Int Ed 12: 245
Tabakovic I (1995) Electrochim Acta 40: 2809
Anderbert P, Bekolo H, Cossy J, Bouzide J (1995) J Electroanl Chem 389: 215
Steckhan E (1987) Topics in Current Chemistry 142: 1
Tabakovic I, Lacan M, Damoni Sh (1976) Electrochim Acta 21: 621
Tabakovic I, Grujic Z (1982) Bull Soc Chim (Belgrade) 47: 339
Kovalesky AC, Shine HJ (1988) J Org Chem 53: 1973
Shin S, Shine HJ (1992) J Org Chem 53: 2706
Dreher EL, Bracht J, El-Mobayed M, Hutter P, Winter W, Rieker A (1982) Chem Ber 115: 288
Grujic Z, Tabakovic I, Sanicanin Z (1989) Croat Chem Acta 62: 5453
Crljenak S, Tabakovic I, Jeremic D, Gaon I (1983) Acta Chem Scand B37: 527
Batusic M, Tabakovic I, Crljenak S (1981) Croat Chem Acta 54: 397
Gunic J, Tabakovic I, Sanicanin Z (1990) Electrochim Acta 35: 225
Sanicanin Z, Juric A, Tabakovic I Trinajstic N (1987) J Org Chem 52: 4053
Sanicanin Z, Tabakovic I (1986) Tetrahedron Lett 27: 407
Sanicanin Z, Tabakovic I (1988) Electrochim Acta 33: 1595
Miljkovic S, Tabakovic I, Sanicanin Z, Cekovic Z (1990) J Serb Chem Soc 55: 131
Sanicanin Z, Tabakovic I, unpublished results
Pandey G, Krishna A, Kumaraswamy G (1987) Tetrahedron Lett 28: 4615
Esker JL, Newcomb M (1993) Adv Heterocyclic Chem 58: 1
Tokuda M, Yamada Y, Takagi T, Suginome H (1985) Tetrahedron Lett 26: 6085
Tokuda M, Yamada Y, Takagi T, Suginome H (1987) Tetrahedron 43: 281
Tokuda M, Miyamoto T, Fujita H, Suginome H (1991) Tetrahedron 47: 747
Karady S, Corley EG, Abramson NL, Weinstock LM (1989) Tetrahedron Lett 30: 2191
Karady S, Corley EG, Abramson NL, Amato JS, Weinstock LM (1991) Tetrahedron 47: 757
Saito K, Hattori M, Sato T, Takahashi K (1992) Heterocycles 34: 129
Lacan M, Rogic V, Tabakovic I, Galijas D, Solomon T (1983) Electrochim Acta 28: 199
Chiba T, Sakagami H, Murata M, Okimoto M (1995) J Org Chem 60: 6764
Uneyama K, Kobayashi M (1994) J Org Chem 59: 3003
Uneyama K, Kobayashi M (1991) Tetrahedron Lett 32: 5981
Becker JY, Zinger B (1982) Tetrahedron 38: 1677
Becker JY, Zinger B (1980) Electrochim Acta 25: 791
Becker JY, Zinger B (1982) J Chem Soc Perkin 2: 395
Becker JY (1985) Isr J Chem 25: 196
Becker JY, Zinger B, Yatziv S (1988) J Org Chem 52: 2783
Becker JY, Yatziv S (1988) J Org Chem 53: 1744
Becker JY, Shakkour E, Sarma JARP (1990) J Chem Soc Chem Commun 1016
Becker JY, Shakkour E, Sarma JARP (1992) J Org Chem 57: 3716
Becker JY, Shakkour E (1993) Tetrahedron 49: 6285
Becker JY, Shakkour E (1994) Tetrahedron 50: 12773
Papandopouls A, Lewale B, Steckhan E, Ginzel K, Nieger M (1991) Tetrahedron 47: 563
Shono T, Matsumura Y, Katoh S, Takeuchi K, Sasa K, Kamada T, Shimizu R (1990) J Am Chem Soc 112: 2368
Abou-Elenien GM, El-Anadouli BE, Baraka RM (1991) J Chem Soc Perkin 1: 1377
Chen C, Shih C, Swenton JS (1986) Tetrahedron Lett 27: 1391
Swenton JS, Shih C, Chen C, Chou C (1990) J Org Chem 55: 2019
Zhang F, Dryhurst G (1991) J Org Chem 56: 7113
Cariou M, Carlier R, Simonet J (1983) J Chem Soc Chem Commun 876
Chiba T, Okimoto M (1992) J Org Chem 57: 1375
Schmittel M (1994) Topics in Current Chemistry 169: 183
Brettle R, Perkin JG (1967) J Chem Soc C: 1352
Lacan M, Tabakovic I (1973) Bull Soc Chim (Belgrade) 38: 297
Lacan M, Tabakovic I, Vukicevic M (1973) Croat Chem Acta 45: 1973
Schäfer H, Al Azrak (1972) Chem Ber 105: 2398
Torii S, Uneyama K, Onishi T, Fujita Y, Ishigiro M, Nishida T (1980) Chem I Lett 1603
Yoshida J, Sakaguchi K, Isoe S (1986) Tetrahedron Lett 28: 6075
Yoshida J, Sakaguchi K, Isoe S (1987) Tetrahedron Lett 28: 667
Yoshida J, Nakatani S, Isoe S (1990) Tetrahedron Lett 31: 2425
Shono T, Chuankamnerdkarn M, Maekawa H, Ishifune M, Kashimura S (1994) Synthesis 895
Nicolaou KC, Petasis NA (1984) Selenium in Natural Product Synthesis, CIS Inc, Philadelphia
Torii S, Uneyama K, Ono M (1980) Tetrahedron Lett 21: 2741; Torii S, Uneyama K, Ono M (1981) J Am Chem Soc 103: 4606
Mihailovic Mlj, Konstantinovic S, Vukicevic R (1987) Tetrahedron Lett 28: 4348
Konstantinovic S, Vukicevic R, Mihailovic MLj (1987) Tetrahedron Lett 28: 6511
Vukicevic R, Konstantinovic S, Mihailovic MLj (1988) J Serb Chem Soc 53: 713
Vukicevic R, Konstantinovic S, Mihailovic MLj (1991) Tetrahedron 47: 859
Töteberg-Kaulen S, Steckhan E (1988) Tetrahedron 44: 4389
Cekovic Z, Tabakovic I, unpublished results; for EGA-catalyzed reactions, see Uneyama K (1987) Topics Curr Chem 142: 167
Cekovic Z, Tabakovic I (1979) Bull Soc Chim (Belgrade) 44: 409
Miller LL, Nordblom GD, Mayeda EA (1972) J Org Chem 37: 916
Raju KVS, Raju PVN, Raju GGV (1990) Bull Electrochem 6: 877
Azzem MA, Zahran M, Hagagg E (1994) Bull Chem Soc Jpn 67: 1390
Shono T (1984) Tetrahedron 40: 811
Shono T (1988) Topics Curr Chem 148: 131
Shono T (1984) in: Electroorganic Chemistry as a New Tool in Organic Synthesis, Springer-Verlag, Berlin
Irie K, Okita M, Wahamatu T, Ban Y (1980) Nouv J Chim 4: 275
Moeller KD, Rothfus SL, Wong PL (1991) Tetrahedron 47: 583
Moeller KD (1986) Topics Curr Chem, this issue
Cornille F, Slomeczynska U, Smith ML, Bensen DD, Moeller KD, Marshall GR (1995) J Am Chem Soc 117: 909
Chiba K, Sonoyama J, Tada M (1995) J Chem Soc Chem Commun 1381
Tabakovic I, Trkovnik M, Batusic M, Tabakovic K (1979) Synthesis 590
Berube D, Cauquis G, Pierre G, Fahmy HM (1982) Electrochim Acta 27: 281
Torii S, Tanaka H, Inokuchi T (1988) Topics in Current Chemistry 148: 154
Kitahara K, Takano Y, Nishi H (1987) Denki Kagaku 7: 1497
Kuhn R, Munzing W (1952) Chem Ber 85: 29
Tabakovic I, Trkovnik M, Galijas D (1978) J Electroanal Chem 86: 241
Henning N, Dassler T, Jugelt W (1981) Z Chem 22: 25
Pechman H, Runge P (1894) Ber 27: 323
Zhivich AB, Koldobskii GI, Ostrovski VA (1991) Khim Geterosikl Soedin 12: 1587
Lacan M, Tabakovic I, Cekovic Z (1974) Tetrahedron 30: 2911
Abou-Elenien G (1994) J Electroanal Chem 357: 301
Gollas B, Speiser B (1992) Angew Chem Int Ed 31: 332
Speiser B, Stahl H (1992) Tetrahedron Lett 33: 4429
Dunsch L, Gollas B, Neudeck A, Petr A, Speiser B, Stahk H (1994) Chem Ber 127: 2423
Wei X, Speiser B (1995) Electrochim Acta 40: 2477
Khmelnitckii LI, Novikov SS, Godovikova TI (1981) Chemistry of Furoxanes. Structure and Synthesis (in Russian) Nauka, Moscow
Jugelt W, Tismer M, Rank M (1983) Z Chem 23: 29
Petrosyan VA, Niyazymbetov ME, Ulyanova EV (1989) Izv Akad Nauk SSSR Ser Khim 7: 1683
Petrosyan VA, Niyazymbetov ME, Ulyanova EV (1989) Izv Akad Nauk SSSR Ser Khim 7: 1687
Petrosyan VA, Niyazymbetov ME, Ulyanova EV (1990) Izv Akad Nauk SSSR Ser Khim 3: 625
Niyazymbetov ME, Ulyanova EV, Petrosyan VA (1990) Izv Akad Nauk SSSR Ser Khim 3: 630
Niyazymbetov ME, Ulyanova EV, Petrosyan VA (1992) Soviet Electrochem 28: 449
Rolfs A, Brosig H, Liebscher J (1995) J Prakt Chem 337: 310
Matsuki T, Hu NX, Otsubo T, Ogura F (1988) Bull Chem Soc Jpn 61: 2117
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Tabaković, I. (1997). Anodic synthesis of heterocyclic compounds. In: Steckhan, E. (eds) Electrochemistry VI Electroorganic Synthesis: Bond Formation at Anode and Cathode. Topics in Current Chemistry, vol 185. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-61454-0_71
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DOI: https://doi.org/10.1007/3-540-61454-0_71
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