Synthesis of Novel 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid Derivatives through the Application of Rongalite: A Synergistic Combination of [2+2+2]- and [4+2]-Cycloaddition Reactions

Sambasivarao Kotha; Shaibal Banerjee

doi:10.1055/s-2007-965946

PAPER

Synthesis of Novel 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid Derivatives through the Application of Rongalite: A Synergistic Combination of [2+2+2]- and [4+2]-Cycloaddition Reactions

Sambasivarao Kotha*, Shaibal Banerjee
Department of Chemistry, Indian Institute of Technology-Bombay, Mumbai, 400 076, India
Fax: +91(22)5723480; e-Mail: srk@chem.iitb.ac.in;

Abstract

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Abstract

An efficient route for the synthesis of several novel 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives has been reported. A synergistic combination of [2+2+2]- and [4+2]-cycloaddition reactions has been used for the synthesis of the desired targets.

Key words

1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid - Rongalite - cycloaddition - amino acids - quinones

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Referenzen

References

1 Kotha S. Sreenivasachary N. J. Indian Inst. Sci. 2001, 81: 277

2 Cardillo G. Gentilucci L. Tolomelli A. Mini-Rev. Med. Chem. 2006, 6: 293

3a Wang W. Cai M. Xiong C. Zhang J. Trivedi D. Hruby VJ. Tetrahedron 2002, 58: 7365

3b Rajesh BM. Iqbal J. Curr. Pharm. Biotechnol. 2006, 7: 247

4a Gibson SE. Guillo N. Tozer MJ. Tetrahedron 1999, 55: 585

4b Kazmierski W. Hruby VJ. Tetrahedron 1988, 44: 697

5a Schiller PW. Nguyen TM. Weltrowska G. Wilkes BC. Marsden BJ. Lemieux C. Chung NN. Proc. Natl. Acad. Sci. U.S.A. 1992, 89: 11871

5b Kazmierski WM. Yamamura HI. Hruby VJ. J. Am. Chem. Soc. 1991, 113: 2275

5c Lazarus LH. Bryant SD. Cooper PS. Guerrini R. Balboni G. Salvadori S. Drug Discovery Today 1998, 3: 284

6a Austin NE. Avenell KY. Boyfield I. Branch CL. Coldwell MC. Hadley MS. Jeffrey P. Johns A. Johnson CN. Nash DJ. Riley GJ. Smith SA. Stacey RC. Stemp G. Thewlis KM. Vong AKK. Bioorg. Med. Chem. Lett. 1999, 9: 179

6b Chen KX. Njoroge FG. Pichardo J. Prongay A. Butkiewicz N. Yao N. Madison V. Girijavallabhan V. J. Med. Chem. 2006, 49: 567

7 Sperlinga E. Kosson P. Urbanczyk-Lipkowska Z. Ronsisvalle G. Carr DB. Lipkowski AW. Bioorg. Med. Chem. Lett. 2005, 15: 2467

8a Grunewald GL. Romero FA. Chieu AD. Fincham KJ. Bhat SR. Criscione KR. Bioorg. Med. Chem. 2005, 13: 1261

8b Grunewald GL. Romero FA. Criscione KR. J. Med. Chem. 2005, 48: 1806

9a Leftheris K. Kline T. Vite GD. Cho YH. Bhide RS. Patel DV. Patel MM. Schmidt RJ. Weller HN. Andahazy ML. Carboni JM. Gullo-Brown JL. Lee FYF. Ricca C. Rose WC. Yan N. Barbacid M. Hunt JT. Meyers CA. Seizinger BR. Zahler R. Manne V. J. Med. Chem. 1996, 39: 224

9b Clerc F.-F. Guitton J.-D. Fromage N. Lelievre Y. Duchesne M. Tocque B. James-Surcouf E. Commercon A. Becquart J. Bioorg. Med. Chem. Lett. 1995, 5: 1779

10a Farina V. Reeves JT. Senanayake CH. Song JJ. Chem. Rev. 2006, 106: 2734

10b O’Reilly NJ. Derwin WS. Lin HC. Synthesis 1990, 550

11a Manabe K. Nobutou D. Kobayashi S. Bioorg. Med. Chem. 2005, 13: 5154

11b Comins DL. Thakker PM. Baevsky MF. Badawi MM. Tetrahedron 1997, 53: 16327

11c Chen HG. Goel OP. Synth. Commun. 1995, 25: 49

11d Jansa P. Machacek V. Bertolasi V. Heterocycles 2006, 68: 59

11e Liu ZZ. Tang YF. Chen SZ. Chin. Chem. Lett. 2001, 12: 947

11f Capilla AS. Romero M. Pujol MD. Caignard DH. Renard P. Tetrahedron 2001, 57: 8297

11g Nicoletti M. O’Hagan D. Slawin AMZ. J. Chem. Soc., Perkin Trans. 1 2002, 116

11h Mash EA. Williams LJ. Pfeiffer SS. Tetrahedron Lett. 1997, 38: 6977

11i Chrzanowska M. Rozwadowska MD. Chem. Rev. 2004, 104: 3341

For literature related to hybrid systems, see:

12a Tietze LF. Schneider G. Wölfling J. Fecher A. Nöbel T. Petersen S. Schuberth I. Wulff C. Chem. Eur. J. 2000, 6: 3755

12b Mehta G. Singh V. Chem. Soc. Rev. 2002, 31: 324

12c Álvaro E. de la Torre MC. Sierra MA. Chem. Eur. J. 2006, 12: 6403

For ‘building block approach’, see:

13a Kotha S. Acc. Chem. Res. 2003, 36: 342

13b Corey EJ. Cheng X.-M. The Logic of Chemical Synthesis John Wiley; New York: 1989.

14a Kotha S. Brahmachary E. Lahiri K. Eur. J. Org. Chem. 2005, 4741

14b Sato Y. Nishimata T. Mori M. J. Org. Chem. 1994, 59: 6133

14c Fray MJ. Allen P. Bradley PR. Challenger CE. Cloiser M. Evans TJ. Lewis ML. Mathias JP. Nichols CL. Po-Ba YM. Snow H. Stefaniak MH. Vuong HV. Tetrahedron 2006, 62: 6869

15 Fringuelli F. Taticchi A. The Diels-Alder Reaction: Selected Practical Methods John Wiley & Sons; Chichester: 2002.

For diversity oriented syntheses, see:

16a Shang S. Tan DS. Curr. Opin. Chem. Biol. 2005, 9: 248

16b Spring DR. Org. Biomol. Chem. 2003, 3867

16c Muhuhi J. Spaller MR. J. Org. Chem. 2006, 71: 5515

17 Kotha S. Ghosh AK. Tetrahedron 2004, 60: 10833

18a Mehta G. Kotha S. Tetrahedron 2001, 57: 625

18b Port M. Lett R. Tetrahedron Lett. 2006, 47: 4677

19a O’Donnell MJ. Plott RL. J. Org. Chem. 1982, 47: 2663

19b Brahmachary E. Ph.D. Thesis IIT-Bombay; India: 2000.

19c Kotha S. Sreenivasachary N. Chem. Commun. 2000, 503

19d Kotha S. Sreenivasachary N. Eur. J. Org. Chem. 2001, 3375