Organic Letters
Letter
pyrrolo[2,1-a]quinolines were obtained in good to excellent
yields representing potentially useful substrates for different
fields of chemistry.
(10) Pirwerdjan, R.; Becker, P.; Bolm, C. Org. Lett. 2015, 17, 5008.
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11) Kiruthika, S. E.; Nandakumar, A.; Perumal, P. T. Org. Lett. 2014,
6, 4424.
12) Yamaoka, Y.; Yoshida, T.; Shinozaki, M.; Yamada, K.; Takasu, K.
1
(
J. Org. Chem. 2015, 80, 957.
ASSOCIATED CONTENT
Supporting Information
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(13) For selected examples, see: (a) Ganihigama, D. U.; Sureram, S.;
Sangher, S.; Hongmanee, P.; Aree, T.; Mahidol, C.; Ruchirawat, S.;
Kittakoop, P. Eur. J. Med. Chem. 2015, 89, 1. (b) Hazra, A.; Mondal, S.;
Maity, A.; Naskar, S.; Saha, P.; Paira, R.; Sahu, K. B.; Paira, P.; Ghosh,
S.; Sinha, C.; Samanta, A.; Banerjee, S.; Mondal, N. B. Eur. J. Med.
Chem. 2011, 46, 2132. (c) Kemnitzer, W.; Kuemmerle, J.; Jiang, S. C.;
Sirisoma, N.; Kasibhatla, S.; Crogan-Grundy, C.; Tseng, B.; Drewe, J.;
Cai, S. X. Bioorg. Med. Chem. Lett. 2009, 19, 3481. (d) Cappelli, A.;
Giuliani, G.; Anzini, M.; Riitano, D.; Giorgi, G.; Vomero, S. Bioorg.
*
S
Experimental procedures and full characterization for all
Med. Chem. 2008, 16, 6850. (e) Hranjec, M.; Starcevic,
́
K.; Piantanida,
AUTHOR INFORMATION
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*
I.; Kralj, M.; Marjanovic, M.; Hasani, M.; Westman, G.; Karminski-
́
Zamola, G. Eur. J. Med. Chem. 2008, 43, 2877. (f) Das, B. P.;
Campbell, J. A.; Samples, F. B.; Wallace, R. A.; Whisenant, L. K.;
Woodard, R. W.; Boykin, D. W., Jr. J. Med. Chem. 1972, 15, 370.
Notes
(g) Le Quesne, P. W.; Dong, Y.; Blythe, T. A. Alkaloids: Chem. Biol.
The authors declare no competing financial interest.
Perspect. 1999, 13, 237. (h) Gribble, G. W. In Comprehensive
Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. S.
V., Eds.; Pergamon Press: New York, 1996; p 207. (i) Janosik, T.;
Bergman, J. In Progress in Heterocyclic Chemistry; Gribble, G. W., Joule,
J. A., Eds.; Pergamon: Amsterdam, 2003; p 140.
REFERENCES
■
(
1) For reviews and selected representative work, see: (a) Johnson,
C. R. Aldrichimica Acta 1985, 18, 3. (b) Reggelin, M.; Zur, C. Synthesis
2
000, 1. (c) Gais, H.-J. Heteroat. Chem. 2007, 18, 472. (d) Harmata,
M. Chemtracts 2003, 16, 660. (e) Okamura, H.; Bolm, C. Chem. Lett.
004, 33, 482. (f) Worch, C.; Mayer, A. C.; Bolm, C. In Organosulfur
2
Chemistry in Asymmetric Synthesis; Toru, T., Bolm, C., Eds.; Wiley-
VCH: Weinheim, 2008; p 209. (g) Zhu, Y.; Loso, M. R.; Watson, G.
B.; Sparks, T. C.; Rogers, R. B.; Huang, J. X.; Gerwick, B. C.; Babcock,
J. M.; Kelley, D.; Hegde, V. B.; Nugent, B. M.; Renga, J. M.; Denholm,
I.; Gorman, K.; DeBoer, G. J.; Hasler, J.; Meade, T.; Thomas, J. D. J.
Agric. Food Chem. 2011, 59, 2950. (h) Park, S. J.; Baars, H.; Mersmann,
S.; Buschmann, H.; Baron, J. M.; Amann, P. M.; Czaja, K.; Hollert, H.;
Bluhm, K.; Redelstein, R.; Bolm, C. ChemMedChem 2013, 8, 217.
(
̈
i) Lucking, U. Angew. Chem., Int. Ed. 2013, 52, 9399. (j) Bizet, V.;
Kowalczyk, R.; Bolm, C. Chem. Soc. Rev. 2014, 43, 2426. (k) Shen, X.;
Hu, J. Eur. J. Org. Chem. 2014, 2014, 4437. (l) Bizet, V.; Hendriks, C.
M. M.; Bolm, C. Chem. Soc. Rev. 2015, 44, 3378.
(
2) For selected recent work, see: (a) Yu, H.; Li, Z.; Dannenberg, C.
A.; Bolm, C. Chem. - Asian J. 2016, 11, 54. (b) Dong, S.; Frings, M.;
Cheng, H.; Wen, J.; Zhang, D.; Raabe, G.; Bolm, C. J. Am. Chem. Soc.
2
016, 138, 2166. (c) Wen, J.; Cheng, H.; Dong, S.; Bolm, C. Chem. -
Eur. J. 2016, 22, 5547. (d) Bohmann, R. A.; Unoh, Y.; Miura, M.;
Bolm, C. Chem. - Eur. J. 2016, 22, 6783.
(
3) The structure for the first N-alkynylated sulfoximine mentioned
in the literature was incorrect. Tanaka, R.; Yamabe, K. J. Chem. Soc.,
Chem. Commun. 1983, 329. For the correction, see: Banert, K.;
Hagedorn, M.; Wutke, J.; Ecorchard, P.; Schaarschmidt, D.; Lang, H.
Chem. Commun. 2010, 46, 4058.
(
4) Wang, L.; Huang, H.; Priebbenow, D. L.; Pan, F.-F.; Bolm, C.
Angew. Chem., Int. Ed. 2013, 52, 3478.
(
(
5) Priebbenow, D. L.; Becker, P.; Bolm, C. Org. Lett. 2013, 15, 6155.
6) Chen, X. Y.; Wang, L.; Frings, M.; Bolm, C. Org. Lett. 2014, 16,
3
(
796.
7) In this study, N-alkynylated sulfoximines 8 and 10 were prepared
(
8) For selected reviews on ynamides, see: (a) DeKorver, K. A.; Li,
H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem.
Rev. 2010, 110, 5064. (b) Evano, G.; Coste, A.; Jouvin, K. Angew.
Chem. 2010, 122, 2902; Angew. Chem., Int. Ed. 2010, 49, 2840.
(
c) Evano, G.; Jouvin, K.; Coste, A. Synthesis 2013, 45, 17. (d) Wang,
X.-N.; Yeom, H.-S.; Fang, L.-C.; He, S.; Ma, Z.-X.; Kedrowski, B. L.;
Hsung, R. P. Acc. Chem. Res. 2014, 47, 560. (e) Cook, A. M.; Wolf, C.
Tetrahedron Lett. 2015, 56, 2377.
(
9) Pirwerdjan, R.; Priebbenow, D. L.; Becker, P.; Lamers, P.; Bolm,
C. Org. Lett. 2013, 15, 5397.
C
Org. Lett. XXXX, XXX, XXX−XXX