Communication
ChemComm
R. Argazzi, S. D. Bryant, Y. Jinsmaa, L. H. Lazarus, L. Negri,
E. Giannini, R. Lattanzi, M. Colucci and G. Balboni, J. Med. Chem.,
2006, 49, 3653; (c) L. Bao, Y. Zou, A. Kirk and M. D. Heagy, J. Phys.
Chem. A, 2017, 121, 9708; (d) P. Nandhikonda and M. D. Heagy,
J. Am. Chem. Soc., 2011, 133, 14972; (e) P. Nandhikonda and
M. D. Heagy, Org. Lett., 2010, 12, 4796; ( f ) C. P. Carvalho,
Z. Dominguez, J. P. Da Silva and U. Pischel, Chem. Commun.,
2015, 51, 2698; (g) K. Jemli, P. Audebert, L. Galmiche, G. Trippe-
Allard, D. Garrot, J. S. Lauret and E. Deleporte, ACS Appl. Mater.
´
Interfaces, 2015, 7, 21763; (h) A. Wrona-Piotrowicz, M. Ciechanska,
´
J. Zakrzewski, R. Metivier, A. Brosseau and A. Makal, Dyes Pigm.,
2016, 125, 331.
2 (a) A. R. Katritzky, S. Ozcan and E. Todadze, Org. Biomol. Chem.,
2010, 8, 1296; (b) K. Baathulaa, Y. Xu and X. Qian, J. Photochem.
Photobiol., A, 2010, 216, 24; (c) T. Yanagisawa, N. Kobayashi,
H. Shimosasa, Y. Kumai, R. Miyatake and M. Oda, Dyes Pigm.,
2017, 136, 859–864.
3 (a) R. P. Robinson, B. J. Cronin, K. M. Donahue, B. P. Jones,
L. L. Lopresti-Morrow, P. G. Mitchell, J. P. Rizzi, L. M. Reeves and
S. A. Yocum, Bioorg. Med. Chem. Lett., 1996, 6, 1725; (b) F. K. Brown,
P. J. Brown, D. M. Bickett, C. L. Chambers, H. G. Davies,
D. N. Deaton, D. Drewry, M. Foley and A. B. McElroy, J. Med. Chem.,
1994, 37, 674.
Scheme 4 DFT calculation.
4 C. Jin, R. Alenazy, Y. Wang, R. Mowla, Y. Qin, J. Q. E. Tan,
N. D. Modi, X. Gu, S. W. Polyak, H. Venter and S. Ma, Bioorg. Med.
Chem. Lett., 2019, 29, 882.
5 L. Song, G.-M. Cao, W.-J. Zhou, J.-H. Ye, Z. Zhang, X.-Y. Tian, J. Li
and D.-G. Yu, Org. Chem. Front., 2018, 5, 2086.
6 G. Naresh, R. Kant and T. Narender, Org. Lett., 2015, 17, 3446.
7 (a) Z. Huang, M. V. Lakshmikantham, M. Lyon and M. P. Cava,
´
J. Org. Chem., 2000, 65, 5413; (b) M. E. Vazquez, J. B. Blanco and
B. Imperiali, J. Am. Chem. Soc., 2005, 127, 1300; (c) M. Sainlos and
B. Imperiali, Nat. Protoc., 2007, 2, 3219.
`
8 (a) A. C. Aragones, N. L. Haworth, N. Darwish, S. Ciampi,
N. J. Bloomfield, G. G. Wallace, I. Diez-Perez and M. L. Coote,
Nature, 2016, 531, 88; (b) K. C. Nicolaou, S. A. Snyder, T. Montagnon
and G. Vassilikogiannakis, Angew. Chem., Int. Ed., 2002, 41, 1668;
(c) E. J. Corey, Angew. Chem., Int. Ed., 2002, 41, 1650; (d) E. Goldstein,
B. Beno and K. N. Houk, J. Am. Chem. Soc., 1996, 118, 6036.
9 (a) P. Wessig and G. Mu¨ller, Chem. Rev., 2008, 108, 2051–2063;
(b) W. Li, L. Zhou and J. Zhang, Chem. – Eur. J., 2016, 22, 1558;
(c) O. J. Diamond and T. B. Marder, Org. Chem. Front., 2017, 4,
891.
10 (a) K. M. Brummond and L. S. Kocsis, Acc. Chem. Res., 2015,
48, 2320; (b) L. S. Kocsis, H. N. Kagalwala, S. Mutto, B. Godugu,
S. Bernhard, D. J. Tantillo and K. M. Brummond, J. Org. Chem., 2015,
80, 11686; (c) L. S. Kocsis and K. M. Brummond, Org. Lett., 2014,
16, 4158.
Scheme 5 Proposed mechanism.
substituted propiolamides and aryl acryoyl chlorides. The main
features of this reaction are listed as follows: (1) without the
utilization of transition metals or high temperatures; (2) readily
available starting materials; (3) operationally simple, insensi-
tive to air and moisture; (4) a wide substrate scope; (5) facile
synthesis of the fluorophore 6-DMN on a gram scale with a
shorter time, fewer steps and less waste disposal. The corres-
ponding works are currently being studied in our laboratory
and will be presented in future publications.
11 L. H. Klemm, T. M. McGuire and K. W. Gopinath, J. Org. Chem.,
1976, 41, 2571.
12 S. Chackalamannil, D. Doller, M. Clasby, Y. Xia, K. Eagen, Y. Lin,
H.-A. Tsai and A. T. McPhail, Tetrahedron Lett., 2000, 41, 4043.
13 E. Ruijter, J. Garcia-Hartjes, F. Hoffmann, L. van Wandelen,
F. de Kanter, E. Janssen and R. Orru, Synlett, 2010, 2485.
14 L. S. Kocsis, E. Benedetti and K. M. Brummond, Org. Lett., 2012,
14, 4430.
We are grateful to the National Natural Science Foundation
of China (No. 51873160), the National Natural Science Founda-
tion for Distinguished Young Scholars (81725021) and the
National Natural Science Foundation for Excellent Young Scho- 15 Z. Fang, Y. Liu, B.-D. Barry, P. Liao and X. Bi, Org. Lett., 2015,
17, 782.
lars (81922065) for their financial support. We are grateful
to Prof. Dr. Chaomei Xiong and Prof. Dr. Lingkui Meng at
16 H. J. Mun, E. Y. Seong, K. H. Ahn and E. J. Kang, J. Org. Chem., 2018,
83, 1196.
Huazhong University of Science and Technology for assistance
with the NMR and mass spectrum, respectively.
17 (a) X. Hu, L. Nie, G. Zhang and A. Lei, Angew. Chem., Int. Ed., 2020,
59, 15238; (b) G. Zhang, Y. Lin, X. Luo, X. Hu, C. Chen and A. Lei,
Nat. Commun., 2018, 9, 1225.
18 (a) P. Nandhikonda and M. D. Heagy, Org. Lett., 2010, 12, 4796;
´
(b) M. E. Vazquez, J. B. Blanco and B. Imperiali, J. Am. Chem. Soc.,
Conflicts of interest
´
2005, 127, 1300; (c) M. E. Vazquez, J. B. Blanco, S. Salvadori,
C. Trapella, R. Argazzi, S. D. Bryant, Y. Jinsmaa, L. H. Lazarus,
L. Negri, E. Giannini, R. Lattanzi, M. Colucci and G. Balboni, J. Med.
Chem., 2006, 49, 3653; (d) P. Venkatraman, T. T. Nguyen, M. Sainlos,
O. Bilsel and L. J. Stern, Nat. Chem. Biol., 2007, 3, 222.
There are no conflicts to declare.
Notes and references
19 K. Baathulaa, Y. Xu and X. Qian, Nat. Protoc., 2011, 6, 1990.
1 (a) P. Nandhikonda and M. D. Heagy, Chem. Commun., 2010, 20 S. Grimme, S. Ehrlich and L. Goerigk, J. Comput. Chem., 2011,
´
46, 8002; (b) M. E. Vazquez, J. B. Blanco, S. Salvadori, C. Trapella,
32, 1456.
Chem. Commun.
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