A novel tert-amino effect based approach to 1,2,3,4-tetrahydroquinoline-2-spirocycloalkanes

Tetrahedron

Volumn 62, Issue 39, 2006, Pages 9146-9152

  Tverdokhlebov, Anton V ^a   Gorulya, Alexander P ^a   Tolmachev, Andrey A ^b   Kostyuk, Alexander N ^c   Chernega, Alexander N ^c   Rusanov, Eduard B ^c  

^a ENAMINE LTD   (Ukraine)

^b TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

Aldehydes; Nitriles; Quinoline; Spiro compounds; tert Amino effect

Indexed keywords

1 METHYL 1,2,3,4 TETRAHYDROSPIRO(QUINOLINE 2,1' CYCLOHEXANE) 3,3 DICARBONITRILE; 1 METHYL 1,2,3,4 TETRAHYDROSPIRO(QUINOLINE 2,1' CYCLOPENTANE) 3,3 DICARBONITRILE; 2 [CYCLOHEXYL(METHYL)AMINO]BENZALDEHYDE DERIVATIVE; ACETONITRILE DERIVATIVE; BENZALDEHYDE DERIVATIVE; CYCLOHEXANE DERIVATIVE; CYCLOPENTANE DERIVATIVE; QUINOLINE DERIVATIVE; SPIROQUINOLINE 2,1' CYCLOPENTANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; KNOEVENAGEL CONDENSATION; PRIORITY JOURNAL; RING CLOSING METATHESIS; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

EID: 33747015267     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.042     Document Type: Article

References (64)

1. Katritzky A.R., Rachwal S., and Rachwal B. Tetrahedron 52 (1996) 15031-15070
2. Kouznetsov V., Palma A., Ewert C., and Varlamov A. J. Heterocycl. Chem. 35 (1998) 761-785
3. Francis C.L., and Ward A.D. Aust. J. Chem. 47 (1994) 2109-2117
4. Williamson N.M., March D.R., and Ward A.D. Tetrahedron Lett. 36 (1995) 7721-7724
5. Pearce C.M., and Sanders J.K.M. J. Chem. Soc., Perkin Trans. 1 (1990) 409-411
6. Morimoto Y., Matsuda F., and Shirahama H. Tetrahedron Lett. 31 (1990) 6031-6034
7. Morimoto Y., Matsuda F., and Shirahama H. Synlett (1991) 201-203
8. Hill M.L., and Raphael R.A. Tetrahedron 46 (1990) 4587-4594
9. Cooper M.A., Francis C.L., Holman J.W., Kasum B., Taverner T., Tiekink E.R.T., and Ward A.D. Aust. J. Chem. 53 (2000) 123-129
10. Steinhagen H., and Corey E.J. Org. Lett. 1 (1999) 823-824
11. Michael J.P. Nat. Prod. Rep. (1997) 605-618
12. Kim W.-G., Kim J.-P., Kim C.-J., Lee K.-H., and Yoo I.-D. J. Antibiot. 49 (1996) 20-25
13. Kim W.-G., Kim J.-P., and Yoo I.-D. J. Antibiot. 49 (1996) 26-30
14. Rakotoson J.H., Fabre N., Jacquemond-Collet I., Hannedouche S., Fouraste I., and Moulis C. Planta Med. 64 (1998) 762-763
15. Houghton P.J., Woldemariam T.Z., Watanabe Y., and Yates M. Planta Med. 65 (1999) 250-254
16. Jacquemond-Collet I., Hannedouche S., Fabre N., Fouraste I., and Moulis C. Phytochemistry 51 (1999) 1167-1169
17. Jacquemond-Collet I., Bessiere J.-M., Hannedouche S., Bertrand C., Fouraste I., and Moulis C. Phytochem. Anal. 12 (2001) 312-319
18. Jacquemond-Collet I., Benoit-Vical F., Valentin A., Stanislas E., Mallie M., and Fouraste I. Planta Med. 68 (2002) 68-69
19. Nakayama H., Ferreira M.E., de Arias A.R., de Bilbao N.V., Torres S., Schinini A., and Fournet A. Phytother. Res. 15 (2001) 630-632
20. Kotera M. Bull. Soc. Chim. Fr. (1989) 370-397
21. Daly J.W. In: Herz W., Grisebach H., and Kirby G.W. (Eds). Progress in the Chemistry of Organic Natural Products Vol. 41 (1982), Springer, Wien 205
22. Prostakov N.S., Kouznetsov V.V., and Stashenko E.E. Khim. Geterotsikl. Soedin. (1989) 1514-1519
23. Chem. Heterocycl. Compd. (Engl. Transl.) 25 (1989) 1267-1271
24. Kouznetsov V.V., Aliev A.E., Palma A.R., Varlamov A.V., and Prostakov N.S. Khim. Geterotsikl. Soedin. (1991) 947-952
25. Chem. Heterocycl. Compd. (Engl. Transl.) 27 (1991) 756-761
26. Kouznetsov V.V., Palma A.R., Fernandes M., Aliev A.E., Shevtsov V.K., Varlamov A.V., and Prostakov N.S. Khim. Geterotsikl. Soedin. (1991) 1350-1353
27. Chem. Heterocycl. Compd. (Engl. Transl.) 27 (1991) 1080-1083
28. Kouznetsov V.V., Palma A., Aliev A.E., Fernandes M., Prostakov N.S., and Varlamov A.V. Khim. Geterotsikl. Soedin. (1993) 784-788
29. Chem. Heterocycl. Compd. (Engl. Transl.) 29 (1993) 671-675
30. Palma A.R., Silva I., Stashenko E., Martinez J.R., and Kouznetsov V. J. Heterocycl. Chem. 36 (1999) 675-680
31. Kouznetsov V.V., Zubkov F.I., Nikitina E.V., and Duarte L.D.A. Tetrahedron Lett. 45 (2004) 1981-1984
32. Zubkov F.I., Nikitina E.V., Kouznetsov V.V., and Duarte L.D.A. Eur. J. Org. Chem. (2004) 5064-5074
33. Palma A., Carrillo C., Stashenko E., Kouznetsov V., Bahsas A., and Amaro-Luis J. Tetrahedron Lett. 42 (2001) 6247-6249
34. Kouznetsov V., Zubkov F., Palma A., and Restrepo G. Tetrahedron Lett. 43 (2002) 4707-4709
35. Palma A., Agredo J.S., Carrillo C., Kouznetsov V., Stashenko E., Bahsas A., and Amaro-Luis J. Tetrahedron 58 (2002) 8719-8727
36. Fischer M., and Wagner F. Chem. Ber. 102 (1969) 3486-3494
37. Ito Y., Miyata S., Nakatsuka M., and Saegusa T. J. Am. Chem. Soc. 103 (1981) 5250-5251
38. Paudler W.W., Zeiler A.G., and Goodman M.M. J. Heterocycl. Chem. 10 (1972) 423-424
39. Knolker H.-J., Boese R., and Hartmann K. Tetrahedron Lett. 32 (1991) 1953-1956
40. Barmettler P., and Hansen H.-J. Helv. Chim. Acta 73 (1990) 1515-1573
41. Hamann L.G., Higuchi R.I., Zhi L., Edwards J.P., Wang X.-N., Marschke K.B., Kong J.W., Farmer L.J., and Jones T.K. J. Med. Chem. 41 (1998) 623-639
42. Dorey G., Lockhart B., Lestage P., and Casara P. Bioorg. Med. Chem. Lett. 10 (2000) 935-939
43. Walter H., Sauter H., and Winkler T. Helv. Chim. Acta 75 (1992) 1274-1280
44. Edwards J.P., Ringgenberg J.D., and Jones T.K. Tetrahedron Lett. 38 (1998) 5139-5142
45. Kobayashi K., Takabatake H., Kitamura T., Morikawa O., and Konishi H. Bull. Chem. Soc. Jpn. 70 (1997) 1697-1699
46. Verboom W., Reinhoudt D.N., Visser R., and Harkema S. J. Org. Chem. 49 (1984) 269-276
47. Nijhuis W.H.N., Verboom W., and Reinhoudt D.N. J. Am. Chem. Soc. 109 (1987) 3136-3138
48. Groenen L.C., Verboom W., Nijhuis W.H.N., Reinhoudt D.N., van Hummel G.J., and Feil D. Tetrahedron 44 (1988) 4637-4644
49. Nijhuis W.H.N., Verboom W., El-Fadl A.A., Harkema S., and Reinhoudt D.N. J. Org. Chem. 54 (1989) 199-208
50. Nijhuis W.H.N., Verboom W., El-Fadl A.A., van Hummel G.J., and Reinhoudt D.N. J. Org. Chem. 54 (1989) 209-216
51. Kelderman E., Noorlander-Bunt H.G., Van Eerden J., Verboom W., and Reinhoudt D.N. Recl. Trav. Chim. Pays-Bas 110 (1991) 115-123
52. Verboom W., and Reinhoudt D.N. Recl. Trav. Chim. Pays-Bas 109 (1990) 311-324
53. Meth-Cohn O., and Suschitzky H. Adv. Heterocycl. Chem. 14 (1972) 211-278
54. Glukhareva T.V., Dyachenko E.V., and Morzherin Yu.Yu. Khim. Geterotsikl. Soedin. (2002) 1610-1611
55. Chem. Heterocycl. Compd. (Engl. Transl.) 38 (2002) 1426-1427
56. Dyachenko E.V., Glukhareva T.V., and Morzherin Yu.Yu. Khim. Geterotsikl. Soedin. (2003) 1737-1738
57. Chem. Heterocycl. Compd. (Engl. Transl.) 39 (2003) 1532-1533
58. Dyachenko E.V., Glukhareva T.V., Nikolaenko E.F., Tkachev A.V., and Morzherin Yu.Yu. Izv. Akad. Nauk, Ser. Khim. (2004) 1191-1198
59. Russ. Chem. Bull. 53 (2004) 1240-1247
60. Tverdokhlebov A.V., Gorulya A.P., Tolmachev A.A., Kostyuk A.N., Chernega A.N., and Rusanov E.B. Synthesis (2005) 2161-2170
61. Tverdokhlebov A.V., Resnyanska E.V., Zavada A.V., Tolmachev A.A., Kostyuk A.N., and Chernega A.N. Tetrahedron 60 (2004) 5777-5783
62. Tverdokhlebov A.V., Zavada A.V., Tolmachev A.A., Kostyuk A.N., Chernega A.N., and Rusanov E.B. Tetrahedron 61 (2005) 9618-9623
63. Neidigh K.A., Avery M.A., Williamson J.S., and Bhattacharyya S. J. Chem. Soc., Perkin Trans. 1 (1998) 2527-2532
64. Saito K., Kambe S., Nakano Y., Sakurai A., and Midorikawa H. Synthesis (1983) 210-212