Tungstophosphoric acid catalyzed synthesis of N-sulfonyl-1,2,3,4-tetrahydroisoquinoline analogs

Ratchanok Pingaew Supaluk Prachayasittikul Somsak Ruchirawat Virapong Prachayasittikul

Citation:  Ratchanok Pingaew, Supaluk Prachayasittikul, Somsak Ruchirawat, Virapong Prachayasittikul. Tungstophosphoric acid catalyzed synthesis of N-sulfonyl-1,2,3,4-tetrahydroisoquinoline analogs[J]. Chinese Chemical Letters, 2013, 24(10): 941-944. shu

Tungstophosphoric acid catalyzed synthesis of N-sulfonyl-1,2,3,4-tetrahydroisoquinoline analogs

    通讯作者: Ratchanok Pingaew,
摘要: An operationally simple and eco-friendly protocol has been developed for the synthesis of N-sulfonyl-1,2,3,4-tetrahydroisoquinolines 3 using the modified Pictet-Spengler reaction of N-sulfonylphenylethylamines 1 and various aldehydes 2 in the presence of tungstophosphoric acid hydrate.

English

  • 
    1. [1] K.W. Bentley, The Isoquinoline Alkaloids, Harwood Academic Publishers, Amsterdam, 1998.[1] K.W. Bentley, The Isoquinoline Alkaloids, Harwood Academic Publishers, Amsterdam, 1998.

    2. [2] J.D. Scott, R.M. Williams, Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics, Chem. Rev. 102 (2002) 1669-1730.[2] J.D. Scott, R.M. Williams, Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics, Chem. Rev. 102 (2002) 1669-1730.

    3. [3] P. Siengalewicz, U. Rinner, J. Mulzer, Recent progress in the total synthesis of naphthyridnomycin and lemonomycin tetrahydroisoquinoline antibiotics (TAAs), Chem. Soc. Rev. 37 (2008) 2676-2690.[3] P. Siengalewicz, U. Rinner, J. Mulzer, Recent progress in the total synthesis of naphthyridnomycin and lemonomycin tetrahydroisoquinoline antibiotics (TAAs), Chem. Soc. Rev. 37 (2008) 2676-2690.

    4. [4] K. Iwasa, M. Moriyasu, Y. Tachibana, et al., Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents, Bioorg. Med. Chem. 9 (2001) 2871-2884.[4] K. Iwasa, M. Moriyasu, Y. Tachibana, et al., Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents, Bioorg. Med. Chem. 9 (2001) 2871-2884.

    5. [5] E.D. Cox, J.M. Cook, The Pictet-Spengler condensation: a new direction for an old reaction, Chem. Rev. 95 (1995) 1797-1842.[5] E.D. Cox, J.M. Cook, The Pictet-Spengler condensation: a new direction for an old reaction, Chem. Rev. 95 (1995) 1797-1842.

    6. [6] E.L. Larghi, M. Amongero, A.B.J. Bracca, T.S. Kaufman, The intermolecular Pictet-Spengler condensation with chiral carbonyl derivatives in the stereoselective syntheses of optically active isoquinoline and indole alkaloids, Arkivoc 12 (2005) 98-153.[6] E.L. Larghi, M. Amongero, A.B.J. Bracca, T.S. Kaufman, The intermolecular Pictet-Spengler condensation with chiral carbonyl derivatives in the stereoselective syntheses of optically active isoquinoline and indole alkaloids, Arkivoc 12 (2005) 98-153.

    7. [7] L.K. Lukanov, A.P. Venkov, N.M. Mollov, Application of the intramolecular aamidoalkylation reaction for the synthesis of 2-arylsulfonyl-1,2,3,4-tetrahydroisoquinolines, Synthesis (1987) 204-206.[7] L.K. Lukanov, A.P. Venkov, N.M. Mollov, Application of the intramolecular aamidoalkylation reaction for the synthesis of 2-arylsulfonyl-1,2,3,4-tetrahydroisoquinolines, Synthesis (1987) 204-206.

    8. [8] G.D. Cuny, Synthesis of (±)-aporphine utilizing Pictet-Spengler and intramolecular phenol ortho-arylation reactions, Tetrahedron Lett. 45 (2004) 5167-5170.[8] G.D. Cuny, Synthesis of (±)-aporphine utilizing Pictet-Spengler and intramolecular phenol ortho-arylation reactions, Tetrahedron Lett. 45 (2004) 5167-5170.

    9. [9] K. Ito, H. Tanaka, Syntheses of 1,2,3,4-tetrahydroisoquinolines from N-sulfonylphenethylamines and aldehydes, Chem. Pharm. Bull. 25 (1977) 1732-1739.[9] K. Ito, H. Tanaka, Syntheses of 1,2,3,4-tetrahydroisoquinolines from N-sulfonylphenethylamines and aldehydes, Chem. Pharm. Bull. 25 (1977) 1732-1739.

    10. [10] H.M. Wang, I.J. Kang, L.C. Chen, Ytterbium triflate-catalysed synthesis of ethyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylates using ethyl chloro(phenylselanyl) acetate, Heterocycles 60 (2003) 1899-1905.[10] H.M. Wang, I.J. Kang, L.C. Chen, Ytterbium triflate-catalysed synthesis of ethyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylates using ethyl chloro(phenylselanyl) acetate, Heterocycles 60 (2003) 1899-1905.

    11. [11] H. Kohno, Y. Sekine, A novel cyclization of electron deficient N-benzenesulfonylb-phenethylamines using ethyl chloro(methylthio)acetate. Synthesis of ethyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylates, Heterocycles 42 (1996) 141-144.[11] H. Kohno, Y. Sekine, A novel cyclization of electron deficient N-benzenesulfonylb-phenethylamines using ethyl chloro(methylthio)acetate. Synthesis of ethyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylates, Heterocycles 42 (1996) 141-144.

    12. [12] C.C. Silveira, C.R. Bernardi, A.L. Braga, T.S. Kaufman, Thioorthoesters in the activated Pictet-Spengler cyclization. Synthesis of 1-thiosubstituted tetrahydroisoquinolines and carbon-carbon bond formation via sulfonyl iminium ions generated from N,S-sulfonyl acetals, Tetrahedron Lett. 44 (2003) 6137-6140.[12] C.C. Silveira, C.R. Bernardi, A.L. Braga, T.S. Kaufman, Thioorthoesters in the activated Pictet-Spengler cyclization. Synthesis of 1-thiosubstituted tetrahydroisoquinolines and carbon-carbon bond formation via sulfonyl iminium ions generated from N,S-sulfonyl acetals, Tetrahedron Lett. 44 (2003) 6137-6140.

    13. [13] G. Pasquale, D. Ruiz, J. Autino, et al., Efficient and suitable preparation of Nsulfonyl-1,2,3,4-tetrahydroisoquinolines and ring analogues using recyclable H6P2W18O62·24H2O/SiO2 catalyst, C. R. Chimie 15 (2012) 758-763.[13] G. Pasquale, D. Ruiz, J. Autino, et al., Efficient and suitable preparation of Nsulfonyl-1,2,3,4-tetrahydroisoquinolines and ring analogues using recyclable H6P2W18O62·24H2O/SiO2 catalyst, C. R. Chimie 15 (2012) 758-763.

    14. [14] G.P. Romanelli, D.M. Ruiz, J.C. Autino, H.E. Giaccio, A suitable preparation of Nsulfonyl-1,2,3,4-tetrahydroisoquinolines and their ring homologs with a reusable Preyssler heteropolyacid as catalyst, Mol. Divers. 14 (2010) 803-807.[14] G.P. Romanelli, D.M. Ruiz, J.C. Autino, H.E. Giaccio, A suitable preparation of Nsulfonyl-1,2,3,4-tetrahydroisoquinolines and their ring homologs with a reusable Preyssler heteropolyacid as catalyst, Mol. Divers. 14 (2010) 803-807.

    15. [15] H. Kohno, K. Yamada, A novel synthesis of isoquinolines containing an electronwithdrawing substituent, Heterocycles 51 (1999) 103-117.[15] H. Kohno, K. Yamada, A novel synthesis of isoquinolines containing an electronwithdrawing substituent, Heterocycles 51 (1999) 103-117.

    16. [16] T. Anknor, G. Hilmersson, Instantaneous deprotection of tosylamides and esters with SmI2/amine/water, Org. Lett. 11 (2009) 503-506.[16] T. Anknor, G. Hilmersson, Instantaneous deprotection of tosylamides and esters with SmI2/amine/water, Org. Lett. 11 (2009) 503-506.

    17. [17] H. Senboku, K. Nakahara, T. Fukuhara, S. Hara, Hg cathode-free electrochemical detosylation of N,N-disubstituted p-toluenesulfonamides: mild, efficient, and selective removal of N-tosyl group, Tetrahedron Lett. 51 (2010) 435-438.[17] H. Senboku, K. Nakahara, T. Fukuhara, S. Hara, Hg cathode-free electrochemical detosylation of N,N-disubstituted p-toluenesulfonamides: mild, efficient, and selective removal of N-tosyl group, Tetrahedron Lett. 51 (2010) 435-438.

    18. [18] J.N.W. Timothy, Alternative synthesis of septic shock candidate 3,4-dihydro-3,3-dimethylisoquinoline N-oxide (MDL 101002) utilizing an improved Pictet-Spengler reaction, J. Org. Chem. 63 (1998) 406-407.[18] J.N.W. Timothy, Alternative synthesis of septic shock candidate 3,4-dihydro-3,3-dimethylisoquinoline N-oxide (MDL 101002) utilizing an improved Pictet-Spengler reaction, J. Org. Chem. 63 (1998) 406-407.

    19. [19] V.L. Ponzo, T.S. Kaufman, The first chiral version of Jackson N-benzyl-N-tosylaminoacetal cyclization. A new enantioselective total synthesis of 1-S-(±)-salsolidine, Tetrahedron Lett. 36 (1995) 9105-9108.[19] V.L. Ponzo, T.S. Kaufman, The first chiral version of Jackson N-benzyl-N-tosylaminoacetal cyclization. A new enantioselective total synthesis of 1-S-(±)-salsolidine, Tetrahedron Lett. 36 (1995) 9105-9108.

    20. [20] J. Dong, X. Shi, J. Yan, et al., Efficient and practical one-pot conversions of Ntosyltetrahydroisoquinolines into isoquinolines and of N-tosyltetrahydro-b-carbolines into b-carbolines through tandem b-elimination and aromatization, Eur. J. Org. Chem. (2010) 6987-6992.[20] J. Dong, X. Shi, J. Yan, et al., Efficient and practical one-pot conversions of Ntosyltetrahydroisoquinolines into isoquinolines and of N-tosyltetrahydro-b-carbolines into b-carbolines through tandem b-elimination and aromatization, Eur. J. Org. Chem. (2010) 6987-6992.

    21. [21] C.C. Silveira, C.R. Bernardi, A.L. Braga, T.S. Kaufman, Desulfonylation of N-sulfonyl tetrahydroisoquinoline derivatives by potassium fluoride on alumina under microwave irradiation: selective synthesis of 3,4-dihydroisoquinolines and isoquinoline, Synlett (2002) 907-910.[21] C.C. Silveira, C.R. Bernardi, A.L. Braga, T.S. Kaufman, Desulfonylation of N-sulfonyl tetrahydroisoquinoline derivatives by potassium fluoride on alumina under microwave irradiation: selective synthesis of 3,4-dihydroisoquinolines and isoquinoline, Synlett (2002) 907-910.

    22. [22] T. Ueda, H. Kotsuki, Heteropoly acids: green chemical catalysts in organic synthesis, Heterocycles 76 (2008) 73-97.[22] T. Ueda, H. Kotsuki, Heteropoly acids: green chemical catalysts in organic synthesis, Heterocycles 76 (2008) 73-97.

    23. [23] G.P. Romanelli, J.C. Autino, Recent applications of heteropolyacids and related compounds in heterocycles synthesis, Mini-Rev. Org. Chem. 6 (2009) 359-366.[23] G.P. Romanelli, J.C. Autino, Recent applications of heteropolyacids and related compounds in heterocycles synthesis, Mini-Rev. Org. Chem. 6 (2009) 359-366.

    24. [24] I.V. Kozhevnikov, Heteropoly acids and related compounds as catalysts for fine chemical synthesis, Catal. Rev. Sci. Eng. 37 (1995) 311-352.[24] I.V. Kozhevnikov, Heteropoly acids and related compounds as catalysts for fine chemical synthesis, Catal. Rev. Sci. Eng. 37 (1995) 311-352.

    25. [25] R. Pingaew, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Synthesis and cytotoxicity of novel 2,2'-bis-and 2,2',2"-tris-indolylmethanes-based bengacarboline analogs, Arch. Pharm. Res. 35 (2012) 949-954.[25] R. Pingaew, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Synthesis and cytotoxicity of novel 2,2'-bis-and 2,2',2"-tris-indolylmethanes-based bengacarboline analogs, Arch. Pharm. Res. 35 (2012) 949-954.

    26. [26] R. Pingaew, A. Worachartcheewan, C. Nantasenamat, et al., Synthesis, cytotoxicity and QSAR study of N-tosyl-1,2,3,4-tetrahydroisoquinoline derivatives, Arch. Pharm. Res. (2013), http://dx.doi.org/10.1007/s12272-013-0111-9.[26] R. Pingaew, A. Worachartcheewan, C. Nantasenamat, et al., Synthesis, cytotoxicity and QSAR study of N-tosyl-1,2,3,4-tetrahydroisoquinoline derivatives, Arch. Pharm. Res. (2013), http://dx.doi.org/10.1007/s12272-013-0111-9.

    27. [27] J.L. Jios, G.P. Romanelli, J.C. Autino, et al., Complete 1H and 13C NMR spectral assignment of N-aralkylsulfonamides, N-sulfonyl-1,2,3,4-tetrahydroisoquinolines and N-sulfonyl-2,3,4,5-tetrahydro-1H-2-benzazepines. Conformational analysis of N-[((3',4'-dichlorophenyl) methyl)sulfonyl]-3-methyl-2,3,4,5-tetrahydro-1H-2-benzazepin, Magn. Reson. Chem. 43 (2005) 1057-1062.[27] J.L. Jios, G.P. Romanelli, J.C. Autino, et al., Complete 1H and 13C NMR spectral assignment of N-aralkylsulfonamides, N-sulfonyl-1,2,3,4-tetrahydroisoquinolines and N-sulfonyl-2,3,4,5-tetrahydro-1H-2-benzazepines. Conformational analysis of N-[((3',4'-dichlorophenyl) methyl)sulfonyl]-3-methyl-2,3,4,5-tetrahydro-1H-2-benzazepin, Magn. Reson. Chem. 43 (2005) 1057-1062.

    28. [28] R. Pingaew, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Synthesis and cytotoxicity of novel N-sulfonyl-1,2,3,4-tetrahydoisoquinoline thiosemicarbazone derivatives, Med. Chem. Res. 22 (2013) 267-277.[28] R. Pingaew, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Synthesis and cytotoxicity of novel N-sulfonyl-1,2,3,4-tetrahydoisoquinoline thiosemicarbazone derivatives, Med. Chem. Res. 22 (2013) 267-277.

    29. [29] A. Javid, M.M. Heravi, F.F. Bamoharram, One-pot three-component synthesis of bacetamido carbonyl compounds catalyzed by heteropoly acids, Monatsh. Chem. 143 (2012) 831-834.[29] A. Javid, M.M. Heravi, F.F. Bamoharram, One-pot three-component synthesis of bacetamido carbonyl compounds catalyzed by heteropoly acids, Monatsh. Chem. 143 (2012) 831-834.

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  0
  • HTML全文浏览量:  0
文章相关
  • 收稿日期:  2013-03-28
  • 网络出版日期:  2013-06-08
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章