Intramolecular sulfoxide electrophilic sulfenylation in 2- and 3-indoleanilides

Tetrahedron

Volumn 63, Issue 49, 2007, Pages 12185-12194

  Eggers, Mary E ^a,b   Jog, Parag V ^a,c   Bates, Dallas K ^a  

^a MICHIGAN TECHNOLOGICAL UNIVERSITY   (United States)

^b Synovo GmbH   (Germany)

^c California Institute of Technology   (United States)

Author keywords

Electrophilic sulfenylation; Indole; Spirocycle; Sulfoxide

Indexed keywords

INDOLE DERIVATIVE; SULFOXIDE;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 35349023135     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.050     Document Type: Article

References (103)

1. For recent reviews see:
2. Lucchi O.D., Miotti U., and Modena G. In: Paquette L.A. (Ed). Organic Reactions Vol. 40 (1991), Wiley, New York, NY 157-405
3. Padwa A., Gunn Jr. D.E., and Osterhout M.H. Synthesis (1997) 1353-1377
4. Padwa A., and Waterson A.G. Curr. Org. Chem. 4 (2000) 175-203
5. Sano T. Trends Heterocycl. Chem. 7 (2001) 117-142
6. Bur S.K., and Padwa A. Chem. Rev. 104 (2004) 2401-2432
7. Pyne S.G., and Hajipour A.R. Tetrahedron 50 (1994) 13501-13510
8. Amat M., Hadida S., Pshenichnyi G., and Bosch J. J. Org. Chem. 62 (1997) 3158-3175
9. Arnone A., Bravo P., Bruche L., Crucianelli M., Zanda M., and Zappala C. J. Chem. Res., Synop. (1997) 416-417
10. Kawasaki T., Suzuki H., Sakaya I., Nakanishi H., and Sakamoto M. Tetrahedron Lett. 38 (1997) 3251-3252
11. Amat M., Llor N., Coll M.C., Casamitjana N., and Bosch J. ARKIVOC (2004) 14-25. http://www.arkat-usa.org/ark/journal/2004/Melendez/EM-755K/755K.pdf
12. Bates D.K., Sell B.A., and Picard J.A. Tetrahedron Lett. 28 (1987) 3535-3538
13. Wang L.X., Soczka-Guth T., Havinga E., and Muellen K. Angew. Chem., Int. Ed. Engl. 35 (1996) 1495-1497
14. Horiguchi Y., Sonobe A., Saitoh T., Toda J., and Sano T. Chem. Pharm. Bull. 49 (2001) 1132-1137
15. Becht J.-M., Wagner A., and Mioskowski C. J. Org. Chem. 68 (2003) 5758-5761
16. Hocker J., Ley K., and Merten R. Synthesis (1975) 334-335
17. Hartke K., Teuber D., and Gerber H.-D. Heterocycles 24 (1986) 2399-2402
18. Hartke K., Teuber D., and Gerber H.-D. Tetrahedron 44 (1988) 3261-3270
19. Wendebourg H.H., and Hartke K. Synthesis (1989) 329-331
20. Feldman K.S. Tetrahedron 62 (2006) 5003-5034
21. 6c,6d)
22. Picard J.A., Chen S., and Bates D.K. Heterocycles 38 (1994) 1775-1789
23. Bates D.K., Winters R.T., and Picard J.A. J. Org. Chem. 57 (1992) 3094-3097
24. Huang H.-Y., Wang H.M., Kang I.-J., and Chen L.-C. J. Chin. Chem. Soc. 50 (2003) 1057-1060
25. Wang H.M., Lin M.C., and Chen L.C. J. Chin. Chem. Soc. 41 (1994) 217-220
26. Chou T.S., Burgtorf J.R., Ellis A.L., Lammert S.R., and Kukolja S.P. J. Am. Chem. Soc. 96 (1974) 1609-1610
27. 3) for addition to alkenes.
28. Morin R.B., Jackson B.G., Mueller R.A., Lavagnino E.R., Scanlon W.B., and Andrews S.L. J. Am. Chem. Soc. 85 (1963) 1896-1897
29. Morin R.B., Jackson B.G., Mueller R.A., Lavagnino E.R., Scanlon W.B., and Andrews S.L. J. Am. Chem. Soc. 91 (1969) 1401-1407
30. Brichard M.H., Musick M., Janousek Z., and Viehe H.G. Synth. Commun. 20 (1990) 2379-2386
31. Some optically active sulfoxides have been shown to racemize (even at room temperature) via a process of syn-β elimination to an achiral sulfenic acid followed by recyclization to racemic sulfoxide:
32. Stoodley R.J., and Wilkins R.B. J. Chem. Soc., Perkin Trans. 1 (1974) 1572-1579
33. Berges D.A., and Taggert J.J. J. Org. Chem. 50 (1985) 413-415 See also:
34. Lee W.S., Hahn H.G., and Nam K.D. J. Org. Chem. 51 (1986) 2789-2795
35. Hoard, D. W.; Luke, W. D. U.S. Patent 5,569,772, 1996;
36. Chem. Abstr. 1996, 126, 7983;
37. Hoard, D. W.; Luke, W. D. U.S. Patent 5,514,826, 1996;
38. Chem. Abstr. 1996, 125, 86485;
39. Aikins, J. A.; Zhang, T. Y. Patent Application WO 96-US9167 19960604, 1996;
40. Chem. Abstr. 1996, 126, 117861;
41. Hoard, D. W.; Luke, W. D.; Johnson, R. A. Book of Abstracts, 214th ACS National Meeting, Las Vegas, NV, September 7-11, 1997; ORGN-326;
42. Zhang, T. Y.; O'Toole, J. C.; Aikins, J.; Sullivan, K. A. Book of Abstracts, 213th ACS National Meeting, San Francisco, CA, April 13-17, 1997; ORGN-175.
43. Bates D.K., Tafel K.A., and Xu J. Heterocycl. Commun. 2 (1996) 115-116
44. Bates D.K., and Xia M. J. Org. Chem. 63 (1998) 9190-9196
45. Bates D.K., and Tafel K.A. J. Org. Chem. 59 (1994) 8076-8080
46. 3,3-Spirocyclic and other 3,3-disubstituted-3H-indolinium species resulting from indole/electrophile interactions are a common occurrence throughout indole chemistry:
47. Jackson A.H., and Smith A.E. Tetrahedron 21 (1965) 989-1000
48. Jackson A.H., Naidoo B., and Smith P. Tetrahedron 24 (1968) 6119-6129
49. Jackson A.H., and Smith A.E. Tetrahedron 24 (1968) 403-413
50. Biswas K.M., and Jackson A.H. Tetrahedron 25 (1969) 227-241
51. Jackson A.H., and Naidoo B. J. Chem. Soc., Perkin Trans. 2 (1973) 548-551
52. Hallett D.J., Gerhard U., Goodacre S.C., Hitzel L., Sparey T.J., Thomas S., Rowly M., and Ball R.G. J. Org. Chem. 65 (2000) 4984-4993
53. Decker M., Faust R., Wedig M., Nieger M., Holzgrabe U., and Lehmann J. Heterocycles 55 (2001) 1455-1466
54. Nippon Chemiphar Co. Ltd, Japanese Patent JP 59,27,870, 1971;
55. Chem. Abstr. 101 (1984) 110729f
56. Alkyl=Et:. Nieforth K.A. J. Pharm. Sci. 52 (1963) 1136-1139
57. 2CN:. Lankin D.C., Petterson R.C., and Velazquez R.A. J. Org. Chem. 39 (1974) 2801-2803
58. Alkyl=tert-Bu:. Courtin A., von Tobel H.-R., and Auerbach G. Helv. Chim. Acta 63 (1980) 1412-1419
59. Kermack W.O., Perkin Jr. W.H., and Robinson R. J. Chem. Soc. 119 (1921) 1602-1642
60. (Chem. Abstr. 1921, 16, 367);
61. Szmuszkovicz J. J. Org. Chem. 29 (1964) 178-184
62. Boatman R.J., and Whitlock H.W. J. Org. Chem. 41 (1976) 3050-3051
63. Bergman J., Carlsson R., and Sjoberg B. J. Heterocycl. Chem. 14 (1977) 1123-1134
64. Augelli-Szafran C.E., Blankley C.J., Roth B.D., Trivedi B.K., Bousley R.F., Essenburg A.D., Hamelehle K.L., Krause B.R., and Stanfield R.L. J. Med. Chem. 36 (1993) 2943-2949
65. Node M., Itoh A., Nishide K., Abe H., Kawabata T., Masaki Y., and Fuji K. Synthesis (1992) 1119-1124
66. Terney Jr. A.L., Chasar D.W., and Sax M. J. Org. Chem. 32 (1967) 2465-2470
67. Terney Jr. A.L., Ens L., Herrmann J., and Evans S. J. Org. Chem. 34 (1969) 940-945
68. Alkyl=Et, prepared using the general procedure of. Barluenga J., Bayon A.M., and Asensio G. J. Chem. Soc., Chem. Commun. (1984) 1334-1335
69. See Section 4;
70. Kuliev A.M., Agaeu A.N., and Mamedov F.A. Ser. Khim. Nauk. (1971) 32-36
71. (Chem. Abstr. 1984, 77, 151594).
72. Gajda T., and Zwierzak A. Synthesis (1981) 1005-1008
73. Both 2-cyanoethyl and tert-butyl sulfoxides are known to undergo both SES-type reactions and sulfenic acid formation at much lower temperatures than methyl or ethyl sulfoxides:. Shelton J.R., and Davis K.E. Int. J. Sulfur Chem. 3 (1973) 205-216
74. Jog P.V., Brown R.E., and Bates D.K. J. Org. Chem. 68 (2003) 8240-8243
75. Oki M. Applications of Dynamic NMR Spectroscopy to Organic Chemistry (1985), VCH, Deerfield Beach, FL
76. Saito S., Toriumi Y., Tomioka N., and Itai A. J. Org. Chem. 60 (1995) 4715-4720
77. Sulfoxide bands in the IR spectra of 2ab and 6ab appear at lower frequency than those of compounds in the amidic NH series:. Furukawa N., and Fujihara H. In: Patai S., Rappoport Z., and Stirling C.J.M. (Eds). The Chemistry of Sulfones and Sulfoxides (1988), John Wiley and Sons, New York, NY 541-565
78. 3 solution in the range 290-365 K) are -1.0 and -5.5 ppb/K, respectively:
79. Soth M.J., and Nowick J.S. J. Org. Chem. 64 (1999) 276-281
80. Gung B.W., Zhu Z., and Everingham B. J. Org. Chem. 62 (1997) 3436-3437
81. Kessler H. Angew. Chem., Int. Ed. Engl. 21 (1982) 512-523
82. Bates D.K., and Habib Q.A. J. Heterocycl. Chem. 32 (1995) 1477-1481
83. Hamel P., Girard M., and Tsou N.N. J. Heterocycl. Chem. 36 (1999) 643-652
84. Ambrogi V., Furlani A., Grandolini G., Papaioannou A., Perioli L., Scarcia V., and Tuttobello L. Eur. J. Med. Chem. 28 (1993) 659-667
85. Atkinson J.G., Hamel P., and Girard Y. Synthesis (1988) 480-481
86. Blade-Font A. Tetrahedron Lett. 21 (1980) 2443-2446
87. Swain C.J., Baker R., Kneen C., Moseley J., Sauders J., Seward E.M., Stevenson G., Beer M., Stanton J., and Waitling K. J. Med. Chem. 34 (1991) 140-151
88. Jackson A.H., Naidoo B., Smith A.E., Bailey A.S., and Vandrevala M.H. J. Chem. Soc., Chem. Commun. (1978) 779-781
89. Engqvist R., and Bergman J. Tetrahedron 59 (2003) 9649-9653
90. Nagarajan K., Arya V.P., Parthasarathy T.N., Shenoy S.J., Shah R.K., and Kulkarni Y.S. Indian J. Chem. Soc., Sect. B 20 (1981) 672-679
91. 5a appears to be roughly the same as an alkylthio group under the same conditions:. Kakushima M., and Frenette R. J. Org. Chem. 49 (1984) 2025-2027
92. Harris R.L.N., and McFadden H.G. Aust. J. Chem. 39 (1986) 887-892
93. Plate R., and Ottenheijm H.C.J. Tetrahedron 42 (1986) 4511-4516
94. Hamel P., Girard Y., and Atkinson J.G. J. Chem. Soc., Chem. Commun. (1989) 63-65
95. Hamel P., Girard Y., and Atkinson J.G. J. Org. Chem. 57 (1992) 2694-2699
96. Wright S.W., Abelman M.M., Bostrom L.L., and Corbett R.L. Tetrahedron Lett. 33 (1992) 153-156
97. Aucagne V., Aversa M.C., Batattucci A., Bonacorsi P., Giannetto P., Rollin P., and Tatibouet A. J. Org. Chem. 67 (2002) 6925-6930
98. Bell R., Cottam P.D., Davies J., and Jones D.N. J. Chem. Soc., Perkin Trans. 1 (1981) 2106-2115
99. Shelton J.R., and Davis K.E. Int. J. Sulfur Chem. 3 (1973) 197-204
100. Kamiya T., Teraji T., Saito Y., Hashimoto M., Nakaguchi O., and Oku T. Tetrahedron Lett. (1973) 3001-3004
101. See also:. Micetich R.G., Maiti S.N., Singh M.P., Tanaka M., Yamazaki T., and Ogawa K. Tetrahedron Lett. 26 (1985) 5971-5977
102. Block E., and O'Connor J. J. Am. Chem. Soc. 96 (1974) 3929-3944
103. Koch P., Ciuffarin E., and Fava A. J. Am. Chem. Soc. 92 (1970) 5971-5977