The Xanthate Route to Indolines, Indoles, and their Aza Congeners.
azaindoles
fluoroazaindoles
indoles
indolines
radicals
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
06 Oct 2020
06 Oct 2020
Historique:
received:
18
03
2020
revised:
17
04
2020
pubmed:
22
4
2020
medline:
22
4
2020
entrez:
22
4
2020
Statut:
ppublish
Résumé
Convergent routes to a variety of indolines, indoles, oxindoles, and their aza analogues involving radical additions of xanthates are described. Three approaches are summarized. The first is the least general and relies on the generation of aryl or heteroaryl radicals starting from diazonium salts. The second involves radical addition to N-allylanilines followed by ring-closure onto the aromatic core. A large variety of indolines and azaindolines can thus be obtained and, in many cases, converted into the corresponding indoles and azaindoles by various methods. The synthesis of novel fluoroazaindolines and fluoroazaindoles by a rare homolytic ipso-substitution of fluorine atoms is particularly noteworthy. The last approach hinges on the direct modification of indoles by radical addition to the pyrrole subunit of the indole nucleus. Application of this methodology to the total synthesis of melatonin and the alkaloids mersicarpine, caulerpine, and the pentacyclic skeleton of tronocarpine is briefly discussed. Most of the compounds described herein would be difficult to obtain by more traditional routes.
Identifiants
pubmed: 32314826
doi: 10.1002/chem.202001341
doi:
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
12689-12705Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
G. W. Gribble, Indole Ring Synthesis: From Natural Products to Drug Discovery, Wiley, New York, 2016;
Heterocyclic Scaffolds II: Reactions and Applications of Indoles (Ed.: G. W. Gribble), Springer, Heidelberg, 2010;
A. R. Katrizky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor, Comprehensive Heterocyclic Chemistry III, Elsevier, Oxford, 2008.
Dictionary of the Alkaloids (Eds.: J. Buckingham, K. H. Baggaley, A. D. Roberts, L. F. Szabó), CRC Press, Boca Raton, 2010.
N. K. Kaushik, N. Kaushik, P. Attri, N. Kumar, C. H. Kim, A. K. Verma, E. H. Choi, Molecules 2013, 18, 6620-6662.
G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875-2911;
Name reactions in Heterocyclic Chemistry, Vols. 1 and 2 (Ed.: J. J. Li), Wiley, Hoboken, 2005.
See for example:
M. Inman, C. J. Moody, Chem. Sci. 2013, 4, 29-41;
M. Inman, C. J. Moody, Chem. Commun. 2011, 47, 788-790;
K. Hisler, A. G. J. Commeureuc, S. Zhou, J. A. Murphy, Tetrahedron Lett. 2009, 50, 3290-3293;
S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 10251-10263.
M. Yan, J. C. Lo, J. T. Edwards, P. S. Baran, J. Am. Chem. Soc. 2016, 138, 12692-12714;
L. Furst, B. S. Matsuura, J. M. R. Narayanam, J. W. Tucker, C. R. J. Stephenson, Org. Lett. 2010, 12, 3104-3107;
S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873-2920.
F. Popowycz, J.-Y. Mérour, B. Joseph, Tetrahedron 2007, 63, 8689-8707;
F. Popowycz, S. Routier, B. Joseph, J.-Y. Mérour, Tetrahedron 2007, 63, 1031-1064;
J. J. Song, J. T. Reeves, F. Gallou, Z. Tan, N. K. Yee, C. H. Senanayake, Chem. Soc. Rev. 2007, 36, 1120-1132.
For reviews, see:
B. Quiclet-Sire, S. Z. Zard, Isr. J. Chem. 2017, 57, 202-217;
B. Quiclet-Sire, S. Z. Zard, Pure Appl. Chem. 2010, 83, 519-551;
B. Quiclet-Sire, S. Z. Zard, Top Curr. Chem. 2006, 264, 201-236; for an account of the discovery of this process, see:
S. Z. Zard, Aust. J. Chem. 2006, 59, 663-668;
S. W. McCombie, B. Quiclet-Sire, S. Z. Zard, Tetrahedron 2018, 74, 4969-4979.
S. Z. Zard, J. Phys. Org. Chem. 2012, 25, 953-964;
S. Z. Zard, Helv. Chim. Acta 2019, 102, e1900134.
F. LeStrat, J. A. Murphy, M. Hughes, Org. Lett. 2002, 4, 2735-2738;
C. Gonzalez Martin, J. A. Murphy, C. R. Smith, Tetrahedron Lett. 2000, 41, 1833-1836;
J. A. Murphy, K. A. Scott, R. S. Sinclair, C. Gonzalez Martin, A. R. Kennedy, N. Lewis, J. Chem. Soc. Perkin Trans. 1 2000, 2395-2408;
G. F. Meijs, A. L. J. Beckwith, J. Am. Chem. Soc. 1986, 108, 5890-5893;
A. N. Abeywickrema, A. L. J. Beckwith, J. Am. Chem. Soc. 1986, 108, 8227-8229.
L. Tournier, S. Z. Zard, Tetrahedron Lett. 2005, 46, 971-973.
M. Newcomb, Tetrahedron 1993, 49, 1151-1176.
A. Gansäuer, M. Seddiqzai, T. Dahmen, R. Sure, S. Grimme, Beil. J. Org. Chem. 2013, 9, 1620-1629;
see also: P. Wipf, J. P. Maciejewski, Org. Lett. 2008, 10, 4383-4386.
T.-M. Ly, B. Quiclet-Sire, B. Sortais, S. Z. Zard, Tetrahedron Lett. 1999, 40, 2533-2536.
S. K. Bagal, L. Tournier, S. Z. Zard, Synlett 2006, 1485-1490.
F. Gagosz, S. Z. Zard, Synlett 2003, 387-389.
F. Bertrand, V. Pevere, B. Quiclet-Sire, S. Z. Zard, Org. Lett. 2001, 3, 1069-1071.
D. Clemente-Tejeda, S. Z. Zard, Synlett 2016, 27, 136-140.
B. Quiclet-Sire, S. Z. Zard, Org. Lett. 2008, 10, 3279-3282.
B. Quiclet-Sire, G. Revol, S. Z. Zard, Org. Lett. 2009, 11, 3554-3557.
F. Gagosz, S. Z. Zard, Org. Lett. 2003, 5, 2655-2657.
S. Han, S. Z. Zard, Org. Lett. 2014, 16, 5386-5389.
M. De Greef, S. Z. Zard, Tetrahedron 2004, 60, 7781-7791.
S. K. Bagal, M. De Greef, S. Z. Zard, Org. Lett. 2006, 8, 147-150.
B. Hawkins, V. L. Paddock, N. Tölle, S. Z. Zard, Org. Lett. 2012, 14, 1020-1023.
B. M. Trost, T. N. Salzmann, K. Hiroi, J. Am. Chem. Soc. 1976, 98, 4887-4902.
C. Mougin, J. Sançon, S. Z. Zard, Heterocycles 2007, 74, 211-218.
B. Sortais, PhD thesis, Ecole Polytechnique, 2002.
M.-P. Denieul, B. Quiclet-Sire, S. Z. Zard, Chem. Commun. 1996, 2511-2512.
For a review on the synthesis of organofluorine derivatives by using xanthate chemistry, see: S. Z. Zard, Org. Biomol. Chem. 2016, 14, 6891-6912.
F. Coppa, F. Fontana, F. Minisci, G. Pianese, P. Tortoreto, L. Zhao, Tetrahedron Lett. 1992, 33, 687-690.
M. Jeanty, J. Blu, F. Suzenet, G. Guillaumet, Org. Lett. 2009, 11, 5142-5145 and references therein;
P. A. Crooks, B. Robinson, Can. J. Chem. 1969, 47, 2061-2067.
E. Bacqué, M. El Qacemi, S. Z. Zard, Org. Lett. 2004, 6, 3671-3674;
E. Bacqué, M. El Qacemi, S. Z. Zard, Heterocycles 2012, 84, 291-299.
Y. Laot, L. Petit, S. Z. Zard, Chem. Commun. 2010, 46, 5784-5786.
M. A. J. Duncton, Med. Chem. Commun. 2011, 2, 1135-1161.
P. Salomon, W. Kosnik, S. Z. Zard, Tetrahedron 2015, 71, 7144-7153.
L. El Kaïm, L. Grimaud, P. Pravin, Molecules 2011, 16, 9261-9273.
L. El Kaïm, L. Grimaud, J. Oble, Angew. Chem. Int. Ed. 2005, 44, 7961-7964;
Angew. Chem. 2005, 117, 8175-8178;
L. El Kaïm, M. Gizolme, L. Grimaud, J. Oble, Org. Lett. 2006, 8, 4019-4021;
L. El Kaïm, M. Gizolme, L. Grimaud, J. Oble, J. Org. Chem. 2007, 72, 4169-4180.
C. Moutrille, S. Z. Zard, Tetrahedron Lett. 2004, 45, 4631-4634.
M. P. Cava, A. A. Deano, J. Am. Chem. Soc. 1959, 81, 4266-4267;
K. Wojciechowski, Synlett 1991, 571-572;
K. Wojciechowski, Eur. J. Org. Chem. 2001, 3587-3605.
G. Sandford, Halogenated Heterocycles: Synthesis Application and Environment (Ed.: J. Iskra), Springer, Berlin, 2012, pp. 1-31;
H. Amii, K. Uneyama, Chem. Rev. 2009, 109, 2119-2183;
C. A. Hargreaves, G. Sanford, R. Slater, D. S. Yufit, J. A. K. Howard, A. Vong, Tetrahedron 2007, 63, 5204-5211.
Y. Laot, L. Petit, S. Z. Zard, Org. Lett. 2010, 12, 3426-3429.
Y. Laot, L. Petit, N. D. M. Tran, S. Z. Zard, Aust. J. Chem. 2011, 64, 416-425.
Z. Liu, L. Qin, S. Z. Zard, Org. Lett. 2014, 16, 2704-2707.
K. C. Nicolaou, C. J. N. Mathison, T. Montagnon, J. Am. Chem. Soc. 2004, 126, 5192-5201.
F. Peng, M. McLaughlin, Y. Liu, I. Mangion, D. M. Tschaen, Y. Xu, J. Org. Chem. 2016, 81, 10009-10015;
U. Tilstam, M. Harre, T. Heckrodt, H. Weinmann, Tetrahedron Lett. 2001, 42, 5385-5387;
I. Ninomiya, T. Kiguchi, C. Hashimoto, D. H. R. Barton, X. Lusinchi, P. Milliet, Tetrahedron Lett. 1985, 26, 4183-4186;
A. B. A. Jansen, J. M. Johnson, J. R. Surtees, J. Chem. Soc. 1964, 5573-5577. See also ref. 1a.
P. Salomon, S. Z. Zard, Org. Lett. 2014, 16, 2926-2929.
H. Rueeger, R. Lueoend, O. Rogel, J.-M. Rondeau, H. Möbitz, R. Machauer, L. Jacobson, M. Staufenbiel, S. Desrayaud, U. Neumann, J. Med. Chem. 2012, 55, 3364-3386.
B. Quiclet-Sire, B. Sortais, S. Z. Zard, Chem. Commun. 2002, 1692-1693.
T. Shioiri, K. Ninomiya, S. Yamada, J. Am. Chem. Soc. 1972, 94, 6203-6205;
P. A. S. Smith, Org. React. 1946, 3, 337-349.
M. Boumédienne, PhD thesis, Ecole Polytechnique, 2011.
E. Tate, S. Z. Zard, Tetrahedron Lett. 2002, 43, 4683-4686.
T. Kaoudi, B. Quiclet-Sire, S. Seguin, S. Z. Zard, Angew. Chem. Int. Ed. 2000, 39, 731-733;
Angew. Chem. 2000, 112, 747-749.
A. Rentería-Gómez, A. Islas-Jácome, E. Díaz-Cervantes, T. Villaseñor-Granados, J. Robles, R. Gámez-Montaño, Bioorg. Med. Chem. Lett. 2016, 26, 2333-2338;
R. E. Gordillo-Cruz, A. Rentería-Gómez, A. Islas-Jácome, C. J. Cortes-García, E. Díaz-Cervantes, J. Robles, R. Gámez-Montaño, Org. Biomol. Chem. 2013, 11, 6470-6476.
A. Biechy, S. Z. Zard, Org. Lett. 2009, 11, 2800-2803.
J. Magolan, C. A. Carson, M. A. Kerr, Org. Lett. 2008, 10, 1437-1440.
Y. M. Osornio, R. Cruz-Almanza, V. Jiménez-Montaño, L. D. Miranda, Chem. Commun. 2003, 2316-2317.
P. López-Mendoza, J. E. Díaz, A. E. Loaiza, L. D. Miranda, Tetrahedron 2018, 74, 5494-5502;
P. E. Reyes-Gutiérrez, R. O. Torres-Ochoa, R. Martínez, L. D. Miranda, Org. Biomol. Chem. 2009, 7, 1388-1396.
M.-G. Braun, G. Castanedo, L. Qin, P. Salvo, S. Z. Zard, Org. Lett. 2017, 19, 4090-4093.
B. Quiclet-Sire, S. Z. Zard, Heterocycles 2010, 82, 263-271.
S. Han, S. Z. Zard, Tetrahedron 2015, 71, 3680-3689.
C. I. Canché Chay, R. Gómez Cansino, C. I. Espitia Pinzón, R. O. Torres-Ochoa, R. Martínez, Mar. Drugs 2014, 12, 1757-1772. See also:
H. Li, X. Liao, Y. Sun, R. Zhou, W. Long, L. Li, L. Gu, S. Xu, ChemistrySelect 2018, 3, 12406-12409.
N. A. Meanwell, J. Med. Chem. 2011, 54, 2529-2591.
E. M. Carreira, T. C. Fessard, Chem. Rev. 2014, 114, 8257-8322.
V. L. Revil-Baudard, J.-P. Vors, S. Z. Zard, Org. Lett. 2018, 20, 3531-3535.
Q. Huang, S. Z. Zard, Org. Lett. 2018, 20, 1413-1416.
R. O. Torres-Ochoa, P. E. Reyes-Gutiérrez, R. Martínez, Eur. J. Org. Chem. 2014, 48-52.
For selected examples, see:
N. J. Race, Q. Yuan, M. S. Sigman, Chem. Eur. J. 2019, 25, 512-515;
Z. Xie, Y. Zhou, W. Zhao, H. Jiao, Y. Chen, Y. Yang, Z. Li, Bioorg. Med. Chem. Lett. 2015, 25, 4557-4561;
G. Iakobson, M. Pošta, P. Beier, Synlett 2013, 24, 855-859;
B. Liégault, I. Petrov, S. I. Gorelsky, K. Fagnou, J. Org. Chem. 2010, 75, 1047-1060;
A. N. C. Lötter, R. Pathak, T. S. Sello, M. A. Fernandes, W. A. L. van Otterlo, C. B. de Koning, Tetrahedron 2007, 63, 2263-2274;
E. Rossi, G. Abbiati, V. Canevari, G. Celentano, E. Magri, Synthesis 2006, 299-304;
J. J. Chen, Y. Wei, J. C. Drach, L. B. Townsend, J. Med. Chem. 2000, 43, 2449-2456;
F. Chan, P. Magnus, E. G. McIver, Tetrahedron Lett. 2000, 41, 835-838.
J. Axon, L. Boiteau, J. Boivin, J. E. Forbes, S. Z. Zard, Tetrahedron Lett. 1994, 35, 1719-1722; see also:
S. Wang, X. Huang, Y. Wen, Z. Ge, X. Wang, R. Li, Tetrahedron 2015, 71, 8117-8122.
B. Quiclet-Sire, S. Z. Zard, Heterocycles 2019, 99, 742-765.
B. Quiclet-Sire, L. Quintero, G. Sanchez-Jimenez, S. Z. Zard, Synlett 2003, 75-78.
S. Han, S. Z. Zard, Org. Lett. 2014, 16, 1992-1995.