Nucleophilic Addition of Lewis Acid Complexed α-Amino Carbanions to Arynes: Synthesis of 1-Aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines

Kamal Nain Singh; Paramjit Singh; Esha Sharma; Yadwinder Singh Deol

doi:10.1055/s-0033-1341239

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(13): 1739-1750
DOI: 10.1055/s-0033-1341239

paper

Nucleophilic Addition of Lewis Acid Complexed α-Amino Carbanions to Arynes: Synthesis of 1-Aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines

Kamal Nain Singh*

Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh 160014, India Fax: +91(172)2545074 eMail: kns@pu.ac.in

,

Paramjit Singh

Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh 160014, India Fax: +91(172)2545074 eMail: kns@pu.ac.in

,

Esha Sharma

Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh 160014, India Fax: +91(172)2545074 eMail: kns@pu.ac.in

,

Yadwinder Singh Deol

Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh 160014, India Fax: +91(172)2545074 eMail: kns@pu.ac.in

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

The direct C-1 arylation of N-methyl-1,2,3,4-tetrahydroisoquinolines via coupling of α-amino carbanions derived from Lewis acid complexed tetrahydroisoquinolines and in situ generated arynes is described. This process provides an easy access to the title compounds and a new synthetic route to (±)-cryptostyline alkaloids.

Key words

arylation - arynes - tetrahydroisoquinolines - cryptostyline alkaloids - Lewis acid complexation

Volltext

Referenzen

References

1a Cheng P, Huang N, Zhang Q, Zheng Y.-T. Bioorg. Med. Chem. Lett. 2008; 18: 2475
1b Chen K.-X, Xie H.-Y, Li Z.-G. Bioorg. Med. Chem. Lett. 2008; 18: 5381

2 Tiwari RK, Singh D, Singh J, Chhiller AK, Chandra R, Verma AK. Eur. J. Med. Chem. 2006; 41: 40
3 Kuo C.-Y, Wu MJ, Kuo Y.-H. Eur. J. Med. Chem. 2006; 41: 940
4 Ludwig M, Hoesl CE, Wanner KT. Eur. J. Med. Chem. 2006; 41: 1003

5a Charifson PS, Wyrick SD, Hoffman AJ, Bowen JP. J. Med. Chem. 1988; 31: 1941
5b Minor DL, Wyrick SD, Charifson PS. J. Med. Chem. 1994; 37: 4317

6 Leander K, Luning B, Ruusa E. Acta Chem. Scand. 1969; 23: 244
7 Naito R, Yonetoka Y, Okamoto Y, Toyoshima A, Ikeda K. J. Med. Chem. 2005; 48: 6597

8a Munchhof MJ, Meyers AI. J. Org. Chem. 1995; 60: 7086
8b Yamato M, Hashigaki K, Qais N. Tetrahedron 1990; 46: 5909

9a Suzuki H, Aoyagi S, Kibayashi C. Tetrahedron Lett. 1995; 36: 6709
9b Berenguer I, Aouad NE, Andujar S, Romero V, Suvire F, Freret T. Bioorg. Med. Chem. 2009; 17: 4968
9c Ishiwata S, Itakura K. Chem. Pharm. Bull. 1968; 16: 778
9d Reeve W, Eareckson WM. J. Am. Chem. Soc. 1950; 72: 5195
9e Gray NM, Cheng BK, Mick SJ, Lair CM, Contreras PC. J. Med. Chem. 1989; 32: 1242
9f Landais Y, Robin J.-P. Tetrahedron 1992; 48: 7185
9g Leander K, Luning B. Tetrahedron Lett. 1968; 9: 1393

10a Gitto R, Barreca ML, Luca LD, Sarro GD, Ferrerri G. J. Med. Chem. 2003; 46: 197
10b Ruchirawat S, Bhavakul V, Chaisupakitsin M. Synth. Commun. 2003; 33: 621

11 Polniaszek RP, Dillard LW. Tetrahedron Lett. 1990; 31: 797
12 Costa BR, Radesca L. Synthesis 1992; 887
13 Abe K, Saitoh T, Horiguchi Y, Utsunomiya I. Biol. Pharm. Bull. 2005; 28: 1355
14 Umetsu K, Asao N. Tetrahedron Lett. 2008; 49: 2722
15 Tokitoh N, Okazaki R. Bull. Chem. Soc. Jpn. 1988; 61: 735
16 Takano S, Suzuki M, Kijima A, Ogasawara K. Chem. Lett. 1990; 315
17 Kurihara K, Yamamoto Y, Miyaura N. Adv. Synth. Catal. 2009; 351: 260
18 Kessar SV, Singh P, Vohra R, Kaur NP, Singh KN. J. Chem. Soc., Chem. Commun. 1991; 568
19 Kessar SV, Singh P. Chem. Rev. 1997; 97: 721
20 Singh KN, Singh P, Singh P, Deol YS. Org. Lett. 2012; 14: 2202

21a Pellissier H, Santelli M. Tetrahedron 2003; 59: 701
21b Wickham PP, Hazen KH, Guo H. J. Org. Chem. 1991; 56: 2045
21c Yoshida H, Fukushima H, Ohshita J. Angew. Chem. Int. Ed. 2004; 43: 3935
21d Matsumoto T, Hosoya T, Katsuki M. Tetrahedron Lett. 1991; 32: 6735
21e Hofmann RW. Dehydrobenzene and Cycloalkynes. Academic Press; New York: 1967
21f Reinecke MG. Tetrahedron 1982; 38: 427

22a Khanapure SP, Biehl ER. J. Org. Chem. 1990; 55: 1471
22b Hofmann RW. Dehydrobenzene and Cycloalkynes . Academic Press; New York: 1967: 134

23a Adejare A, Miller DD. Tetrahedron Lett. 1984; 25: 5597
23b Kress TH, Leanna MR. Synthesis 1988; 803

24 All new products were characterized by ¹H NMR, ¹³C NMR, IR spectroscopy, and mass spectrometry (APCI-MS and HRMS).
25 Ebden MR, Simpkins NS, Fox DN. Tetrahedron Lett. 1995; 36: 8697

26a Whaley WM, Govindachari TR. Org. React. 1951; 6: 151
26b Marsden R, MacLean DB. Can. J. Chem. 1984; 62: 1392
26c Miller RB, Tsang T. Tetrahedron Lett. 1988; 29: 6715

27 Jones EP, Jones P, Barrett AG. Org. Lett. 2011; 13: 1012
28 Logullo FM, Seitz AM, Friedman L. Org. Synth. 1968; 48: 12
29 Gilman H, Gorsich RD. J. Am. Chem. Soc. 1957; 79: 2625

30a Kessar SV, Singh P, Singh KN, Venugopalan P, Kaur A, Mahendru M, Kapoor R. Tetrahedron Lett. 2005; 46: 6753
30b Blagg J, Coote SJ, Davies SG. J. Chem. Soc., Perkin Trans. 1 1987; 689
30c Ito Y, Nakatsuka M, Saegusa T. J. Am. Chem. Soc. 1982; 104: 7609

31 Bordwell FG, Vanier NR, Zhang X. J. Am. Chem. Soc. 1991; 113: 9856

Many arylation procedures using transition metals, and thus having an obvious drawback are reported.

32a Morrell DC, Kochi JK. J. Am. Chem. Soc. 1975; 97: 7262
32b Milstein D, Stille JK. J. Am. Chem. Soc. 1979; 101: 4992
32c Peng S, Quing FL, Li Y.-Q, Hu C.-M. J. Org. Chem. 2000; 65: 694
32d Gray M, Andrews IP, Hook DF, Kitteringham J, Voyle M. Tetrahedron Lett. 2000; 41: 6237
32e Yus M, Gomis J. Eur. J. Org. Chem. 2002; 1989
32f Campeau L.-C, Fagnou K. Chem. Commun. 2006; 1253
32g Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
32h McGlacken GP, Bateman LM. Chem. Soc. Rev. 2009; 38: 2447
32i Bellina F, Rossi R. Tetrahedron 2009; 65: 10269
32j Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
32k Daugulis O. Top. Curr. Chem. 2010; 292: 57
32l Ackermann L, Vicente R. Top. Curr. Chem. 2010; 292: 211
32m Bouffard J, Itami K. Top. Curr. Chem. 2010; 292: 231

33a Veber DF, Lwowski W. J. Am. Chem. Soc. 1964; 86: 4152
33b Fraser RR, Renaud RN. Can. J. Chem. 1971; 49: 746

34 Gámez-Montaño R, Chávez MI, Roussi G, Cruz-Almanza R. Tetrahedron Lett. 2001; 42: 9
35 Furniss BS. Vogel’s Textbook of Practical Organic Chemistry . 4th ed. ELBS/Longman; London: 1978: 266
36 Fagan PJ, Nugent WA. Org. Synth. Coll. Vol. 9. Wiley; New York: 1998: 653
37 Blagg J, Coote JS, Davies SG, Mobbs BE. J. Chem. Soc., Perkin Trans 1 1986; 2257

38a Bearss DJ, Grand CL. PCT Int. Appl WO2008055233, 2008 ; Chem. Abstr. 2008, 148, 538306.
38b Yu Q, Jin Y, Zhou Z.-Y, Tian W, Long Y.-Q. Bioorg. Med. Chem. Lett. 2006; 16: 5864
38c Roy SC, Rana KK, Guin C, Banerjee B. Synlett 2003; 221

39 Furniss BS. Vogel’s Textbook of Practical Organic Chemistry . 4th ed. ELBS/Longman; London: 1978: 755
40 Kajita M, Niwa T, Fujisaki M, Ueki M, Niimura K. J. Chromatogr. B 1995; 669: 345
41 Bender C, Liebscher J. ARKIVOC 2009; (vi): 111
42 Valpuesta M, Ariza M, Diaz A, Suau R. Eur. J. Org. Chem. 2010; 23: 4393
43 Ahluwalia GS, Narang KS, Rây JN. J. Chem. Soc. 1931; 2057
44 Samano V, Ray JA, Thompson JB, Mook RA, Feldman PL. Org. Lett. 1999; 1: 1993
45 Joachim K. Arch. Pharm. (Weinheim, Germany) 1959; 292: 652
46 Hoshino O, Tanahashi R, Okada M, Akita H, Oishi T. Tetrahedron: Asymmetry 1993; 4: 933
47 Gunzinger J, Leander K. PCT Int. Appl WO 2005087743 A1 20050922, 2005 ; Chem. Abstr. 2005, 143, 326227.
48 Beaven GH, Hassan M, Johnson EA, Klassen NV. J. Chem. Soc. 1961; 2749

Zusatzmaterial

Supporting Information