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2004 | 2 | 1 | 234-246
Tytuł artykułu

Amidoalkylation of heteroaromatic compounds with adducts of acyl chlorides and 3,4-dihydroisoquinoline and isoquinoline

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The N-acyliminium intermediates of 3,4-dihydroisoquinoline and salts of isoquinoline with acyl chlorides were successfully used as amidoalkylating reagents toward synthesis of heterocyclic aromatics as indole, pyrrole, thiophene and pyrazine.
Słowa kluczowe
Wydawca

Czasopismo
Rocznik
Tom
2
Numer
1
Strony
234-246
Opis fizyczny
Daty
wydano
2004-03-01
online
2004-03-01
Twórcy
  • Department of Organic Chemistry, University of Plovdiv, 4000, Plovdiv, Bulgaria, donova@argon.acad.bg
  • Department of Organic Chemistry, University of Plovdiv, 4000, Plovdiv, Bulgaria
  • Department of Organic Chemistry, University of Plovdiv, 4000, Plovdiv, Bulgaria
Bibliografia
  • [1] B.C. Uff, Y. Ho and D.W. Burford: “Formation of Reissert Analogs from Benzimidazole and Use of Carboxylic Acids in a Retro-Reissert Reaction [1]”, J. Heterocyclic Chem., Vol. 24, (1987), pp. 1349–1351; http://dx.doi.org/10.1002/jhet.5570240523[Crossref]
  • [2] H.R. Yajnanarayana, J. Gibson and H.W. Gibson: “Synthesis of 2-Cyano-1,3-dibenzoyl-2,3-dihydrobenzimidazole: A Novel Reissert Compound from Benzimidazole”, J. Org. Chem., Vol. 56, (1991), pp. 865–867; http://dx.doi.org/10.1021/jo00002a071[Crossref]
  • [3] M.A.G. Berg and H.W. Gibson: “Cyanoacylation of 1-Substituted Isoquinolines and 3,4-Dihydroisoquinolines”, J. Org. Chem., Vol. 57, (1992), pp. 748–750; http://dx.doi.org/10.1021/jo00028a064[Crossref]
  • [4] A. Jonczyk and U. Lorencewicz-Pakulska: “Condensation of 2-Benzoyl-1-cyano-1,2-dihydroisoquinoline with Electrophilic Alkenes Under Phase-transfer Catalytic (PTS) Conditions”, J. Chem. Research (S), (1998), pp. 262–263.
  • [5] W.N. Speckamp and H Hiemstra: “Intramolecular reactions of N-acyliminium intermediates”, Tetrahedron, Vol. 41, (1985), pp. 4367–4416; http://dx.doi.org/10.1016/S0040-4020(01)82334-6[Crossref]
  • [6] M.D. Rozwadowska: “Recent progress in the enantioselective synthesis of isoquinoline alkaloids”, Heterocycles, Vol. 39, (1994), pp. 903–931;
  • [7] K.T. Wanner and I. Praschak: “Asymmetric electrophilic α-amidoalkylation 61: Syntheses of tetrahydroisoquinolines of high enantiomeric purity”, Heterocycles, Vol. 29, (1989), pp. 29–33; [Crossref]
  • [8] D.L. Comins and M. Badawi: “Nucleophilic addition to homochiral N-acylisoquinolinium salts. Asymmetric synthesis of (+)-carnegine”, Heterocycles, Vol. 32, (1991), pp. 1869–1873; http://dx.doi.org/10.3987/COM-91-5780[Crossref]
  • [9] K.T. Wanner and F. Paintner: “Asymmetric electrophilic α-amidoalkylation- 10: A new Camphorimide derived chiral auxiliary for the asymmetric synthesis with N-acyliminium ions-preparation of aracemic 2-substituted piperidines”, Tetrahedron, Vol. 50, (1994), pp. 3113–3122. http://dx.doi.org/10.1016/S0040-4020(01)81110-8[Crossref]
  • [10] A.P. Venkov, St.M. Statkova and I. Ivanov: “Synthesis of 1-Phenyl-2-Acyl-Tetrahydroisoquinolines by Intramolecular α-Amidoalkylation Reaction”, Synth. Commun., Vol. 22, (1992), pp. 125–134;
  • [11] A.P. Venkov and St.M. Statkova-Abeghe: “Application of the Intramolecular α-Amidoalkylation Reaction for the Synthesis of Tertiary Amides and 1-Substituted 2-Acyltetrahydroisoquinolines. Synthesis of Carnegine”, Synth. Commun., Vol. 25(2), (1995), pp. 1817–1824;
  • [12] A.P. Venkov and St.M. Statkova-Abeghe: “Synthesis of 1-(2-Oxoalkyl)-2-Acyltetrahydroisoquinolines by α-Amidoalkylation of Methylene Active Carbonyl compounds with N-Acyliminium Intermediates” Synth. Commun., Vol. 26(11), (1996), pp. 2135–2144.
  • [13] A.K. Sheinkman: “Гетарилирование органических соединений”, Khimia Hetrocycl. Soedin., Vol. 1, (1974), pp. 3–18.
  • [14] H. Dobeneck and W. Goltzsche: “Reactionen von N-Acyl-cyclimmonium-Salzen mit nucleophilen Verbindungen”, Chem. Ber., Vol. 95, (1962), pp. 1484–1492.
  • [15] A.K. Sheinkman and A.A. Deikalo: “Реакции цикламмониевьх катионов XV Гетарилирование пирролов N- ацияьнами цолыами хинолиниja, изохинолиниja и акридиниjq”, Khimia Hetrocycl. Soedin., Vol. 7(12), (1972), pp. 1654–1659, (in Russion); “Reactions of Cyclammonium Cations. XV. Hetarylation of Pyrroles by N-Acyl Salts of Isoquinolinium and Acridinium”, Chem. Abstr., Vol. 77, (1972), 5310a.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02476193
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