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

• Authors: Atanas Venkov , Stela Statkova-Abeghe , Atanaska Donova
• Languages of publication: EN

Abstracts

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.

Keywords

EN

isoquinoline; amidoalkylation; heterocycles

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2004
• Volume: 2
• Issue: 1
• Pages: 234-246

Dates

published

1 - 3 - 2004

online

1 - 3 - 2004

Contributors

author

Atanas Venkov

• Department of Organic Chemistry, University of Plovdiv, 4000, Plovdiv, Bulgaria

author

Stela Statkova-Abeghe

• Department of Organic Chemistry, University of Plovdiv, 4000, Plovdiv, Bulgaria

author

Atanaska Donova

• Department of Organic Chemistry, University of Plovdiv, 4000, Plovdiv, Bulgaria

References

• [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.

Identifiers

DOI

10.2478/BF02476193