Synthesis and Characterization of N-Substituted Tetrahydroiso-quinoline Derivatives via a Pictet-Spengler Condensation

Authors

  • Heta A. Patel The Maharaja Sayajirao University of Baroda
  • Arun L. Patel The Maharaja Sayajirao University of Baroda

DOI:

https://doi.org/10.6000/1929-5030.2014.03.03.5

Keywords:

Tetrahydroisoquinoline, Pictet-Spengler reaction, Imine, Trifluoroacetic acid.

Abstract

Synthesis of N-substituted 1,2,3,4 –tetrahydroisoquinoline derivatives and bis-isoquinoline has been carried out via a Pictet-Spengler condensation. Tetrahydroisoquinolines were obtained from 2-(3',4'-dimethoxyphenyl) ethylamine in four steps. The entire synthesized compounds were characterized by IR, 1H NMR and mass spectral data.

Author Biographies

Heta A. Patel, The Maharaja Sayajirao University of Baroda

Chemistry

Arun L. Patel, The Maharaja Sayajirao University of Baroda

Chemistry

References


[1] Locher C, Peerzada N Synthesis of some N-methyl-1,2,3,4- tetrahydroisoquinolines by Friedel–Crafts cyclisation using benzotriazole auxiliary. Chem Soc Perkin Trans 1 1999; 179- 84. http://dx.doi.org/10.1039/a807543c
[2] He Y, Nikulin VI, Vansal SS, Feller DR, Miller DD. Synthesis and human -adrenoceptor activity of 1-(3,5-diiodo-4- methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol derivatives in vitro. J Med Chem 2000; 43: 591-8. http://dx.doi.org/10.1021/jm990463j
[3] Lees GJ. Pharmacology of AMPA/kainate receptor ligands and their therapeutic potential in neurological and psychiatric disorders. Drugs 2000; 59: 33-78. http://dx.doi.org/10.2165/00003495-200059010-00004
[4] Lin Z, Kabada PK. Molecular targets for the rational design of antiepileptic drugs and related neuroprotective agents. Med Res Rev 1997; 17: 537-72. http://dx.doi.org/10.1002/(SICI)1098- 1128(199711)17:63.0.CO;2-2
[5] Rogawski MA, Donevan SD. AMPA receptors in epilepsy and as targets for antiepileptic drugs. Adv Neurol 1999; 79: 947- 63. http://www.ncbi.nlm.nih.gov/pubmed/10514878
[6] Gitto R, Barreca ML, De Luca L, et al. Discovery of a novel and highly potent noncompetitive AMPA receptor antagonist. J Med Chem 2003; 46: 197-00. http://dx.doi.org/10.1021/jm0210008
[7] Kaur J, Ghosh NN, Chandra R. Synthesis and antispasmodic activity evaluation of bis-(papaverine) analogues. Chem Pharm Bull 2004; 52: 316-21. http://dx.doi.org/10.1248/cpb.52.316
[8] Chandra R, Kaur J, Talwar A, Ghosh NN. Synthesis and antispasmodic effect of aryl substituted N-carbamoyl/ thiocarbamoyl isoquinolines. Arkivoc 2001; (viii): 129-35. http://dx.doi.org/10.3998/ark.5550190.0002.814
[9] Kaur J, Ghosh NN, Talwar A, Chandra R. Synthesis of NSubstituted Piperazinyl Carbamoyl and Acetyl Derivatives of Tetrahydropapaverine: Potent Antispasmodic Agents. Chem Pharm Bull 2002; 50: 1223-8. http://dx.doi.org/10.1248/cpb.50.1223
[10] Kitamura M, Hsiao Y, Otha M, et al. General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAPruthenium(I1) complexes. J Org Chem 1994; 59: 297-310. http://dx.doi.org/10.1021/jo00081a007
[11] Scott JD, Williams RM. Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics. Chem Rev 2002; 102: 1669-730. http://dx.doi.org/10.1021/cr010212u
[12] Iwasa K, Moriyasu M, Tachibana Y, et al. Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents. Bioorg Med Chem 2001; 9: 2871-4. http://dx.doi.org/10.1016/S0968-0896(01)00154-7
[13] Minor DL, Wyrick SD, Charifson PS, Watts VJ, Nichols DE, Mailman RB. Synthesis and molecular modeling of 1-phenyll,2,3,4-tetrahydroisoquinolines and related 5,6,8,9-tetrahydro- 13bH-dibenzo
[a,h]quinolizineass D1 dopamine antagonists. J Med Chem 1994; 37: 4317-28. http://dx.doi.org/10.1021/jm00051a008
[14] Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase1 . J Nat Prod 1991; 54: 143-54. http://dx.doi.org/10.1021/np50073a012
[15] Pham VC, Ma J, Thomas SJ, Xu Z, Hecht SM. Alkaloids from alangium javanicum and alangium grisolleoides that mediate Cu2+-dependent DNA strand scission. J Nat Prod 2005; 68: 1147-52. http://dx.doi.org/10.1021/np058013j
[16] Oku N, Matsunaga S, van Soest RWM, Fusetani N. Renieramycin J, a highly cytotoxic tetrahydroisoquinoline alkaloid, from a marine sponge Neopetrosia sp1 . J Nat Prod 2003; 66: 1136-9. http://dx.doi.org/10.1021/np030092g
[17] Naito R, Yonetoku Y, Okamoto Y, Toyoshima A, Ikeda K, Takeuchi M. Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists1 . J Med Chem 2005; 48: 6597-606. http://dx.doi.org/10.1021/jm050099q
[18] Castro L, Ball RG, Broughton HB, et al. Controlled modification of acidity in cholecystokinin B receptor antagonists: N-(1,4-Benzodiazepin-3-yl)-N -
[3-(tetrazol-5- ylamino)phenyl]ureas. J Med Chem 1996; 39: 842-9. http://dx.doi.org/10.1021/jm9506736
[19] Nakamura S, Tanaka M, Taniguchi T, Uchiyama M, Ohwada T. Stereoselectivity of superacid-catalyzed pictet-spengler cyclization reactions. Org Lett 2003; 5: 2087-90. http://dx.doi.org/10.1021/ol034526a
[20] Cox ED, Cook JM. The Pictet-Spengler condensation: a new direction for an old reaction. Chem Rev 1995; 95: 1797-842. http://dx.doi.org/10.1021/cr00038a004
[21] Semple G, Ryder H, Rooker DP, et al. (3R)-N-(1-(tertButylcarbonylmethyl)-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4- benzodiazepin-3-yl)-N’-(3-(methylamino)phenyl)urea (YF476): A potent and orally active gastrin/CCK-B antagonist. J Med Chem 1997; 40: 331-41. http://dx.doi.org/10.1021/jm960669+
[22] March J. Advanced Organic Chemistry: Reactions, Mechanisms and Structure. New York: John Wiley & Sons, 4th ed 1992.
[23] Larghi EL, Amongero M, Bracca ABJ, Kaufman TS. The intermolecular Pictet-Spengler condensation with chiral carbonyl derivatives in the stereoselective syntheses of optically active isoquinoline and indole alkaloids. Arkivoc 2005; (vii): 98-153. http://dx.doi.org/10.3998/ark.5550190.0006.c09

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Published

2014-09-18

How to Cite

Patel, H. A., & Patel, A. L. (2014). Synthesis and Characterization of N-Substituted Tetrahydroiso-quinoline Derivatives via a Pictet-Spengler Condensation. Journal of Applied Solution Chemistry and Modeling, 3(3), 169–174. https://doi.org/10.6000/1929-5030.2014.03.03.5

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General Articles