COMMUNICATIONS
Chem. Commun. 2009, 2562–2564; d) Q. Cai, G. Liang,
References
Y. Xu, X. Qian, W. Zhu, RSC Adv. 2016, 6, 60996–
61000; e) E. M. Sánchez-Carnerero, R. Sandoval-Tor-
rientes, J. Urieta-Mora, F. Moreno, B. L. Maroto, S.
de la Moya, React. Funct. Polym. 2017, 113, 23–30.
[9] a) S. Kobayashi, Chem.-An Asian J. 2016, 11, 425–436;
b) T. Tsubogo, H. Oyamada, S. Kobayashi, Nature 2015,
520, 329–332; c) H. Ishitani, Y. Saito, T. Tsubogo, S.
Kobayashi, Org. Lett. 2016, 18, 1346–1349.
[10] For reviews, see: a) J. Wegner, S. Ceylan, A. Kirschning,
Chem. Commun. 2011, 47, 4583–4592; b) J. C. Pastre,
D. L. Browne, S. V. Ley, Chem. Soc. Rev. 2013, 42,
8849–8869; c) M. B. Plutschack, B. Pieber, K. Gilmore,
P. H. Seeberger, Chem. Rev. 2017, 117, 11796–11893;
d) F. M. Akwi, P. Watts, Chem. Commun. 2018, 54,
13894–13928.
[11] After first step flow, the crude product was obtained by
removing 1,2-dichloroethane under rotary evaporator and
high vacuum for 30 minutes. After that THF solution of
the crude was directly subjected to the second step flow.
This simple technique of solvent exchange was employed
to remove 1,2-dichloroethane which is not a good solvent
for second step considering regioselectivity of target
pyrazole as well as solubility issue of methyl hydrazine.
[12] For selected examples, see: a) F. Giornal, S. Pazenok, L.
Rodefeld, N. Lui, J. P. Vors, F. R. Leroux, J. Fluorine
Chem. 2013, 152, 2–11; b) J. Jaunzems, M. Braun, Org.
Process Res. Dev. 2014, 18, 1055–1059.
[1] For reviews, see: a) V. L. M. Silva, J. Elguero, A. M. S.
Silva, Eur. J. Med. Chem. 2018, 156, 394–429; b) K.
Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y. N. Mabkhot,
F. A. Al-Aizari, M. Ansar, Molecules 2018, 23, 1–85. For
selected references, see: c) S. Fustero, R. Román, J. F.
Sanz-Cervera, A. Simón-Fuentes, A. C. Cuñat, S. Villa-
nova, M. Murguía, J. Org. Chem. 2008, 73, 3523–3529;
d) J. M. Kremsner, M. Rack, C. Pilger, C. Oliver Kappe,
Tetrahedron Lett. 2009, 50, 3665–3668.
[2] For selected examples, see: a) J. Comas-Barceló, D.
Blanco-Ania, S. A. M. W. Van Den Broek, P. J. Nieuw-
land, J. P. A. Harrity, F. P. J. T. Rutjes, Catal. Sci.
Technol. 2016, 6, 4718–4723; b) J. S. Poh, D. L. Browne,
S. V. Ley, React. Chem. Eng. 2016, 1, 101–105; c) J.
Britton, T. F. Jamison, Angew. Chem. Int. Ed. 2017, 56,
8823–8827; Angew. Chem. 2017, 129, 8949–8953; d) J.
Britton, T. F. Jamison, Eur. J. Org. Chem. 2017, 2017,
6566–6574; e) S. B. Ötvös, Á. Georgiádes, D. Ozsvár, F.
Fülöp, RSC Adv. 2019, 9, 8197–8203; f) M. Kandasamy,
B. Ganesan, M.-Y. Hung, W.-Y. Lin, Eur. J. Org. Chem.
2019, 3183–3189; g) V. K. Sthalam, A. K. Singh, S.
Pabbaraja, Org. Process Res. Dev. 2019, DOI: 10.1021/
acs.oprd.9b00212.
[3] a) J. L. Huppatz, Aust. J. Chem. 1983, 36, 135–147;
b) G. Menozzi, L. Mosti, P. Schenone, J. Heterocycl.
Chem. 1987, 24, 1669–1675; c) L. Cheng, Z. H. Shen,
T. M. Xu, C. X. Tan, J. Q. Weng, L. Han, W. L. Peng,
X. H. Liu, J. Heterocycl. Chem. 2018, 55, 946–950.
[4] R. G. Jones, J. Am. Chem. Soc. 1951, 73, 3684–3686.
[5] a) L. Crombie, D. E. Games, A. W. G. James, J. Chem.
Soc. Perkin Trans. 1 1979, 464–471; b) M. V. Pryadeina,
Y. V. Burgart, V. I. Saloutin, P. A. Slepukhin, O. N.
Kazheva, G. V. Shilov, O. A. D’yachenko, O. N. Chupa-
khin, Russ. J. Org. Chem. 2007, 43, 945–955; c) S.
Kobayashi, T. Kinoshita, H. Uehara, T. Sudo, I. Ryu,
Org. Lett. 2009, 11, 3934–3937; d) Y. S. Kudyakova,
D. N. Bazhin, M. V Goryaeva, Y. V Burgart, V. I.
Saloutin, Russ. Chem. Rev. 2014, 83, 120–142.
[13] For selected examples, see: Patent WO 01/46172A1,
a) R. C. Lemoine, A. C. Petersen, L. Setti, A. Jekle, G.
Heilek, A. Derosier, C. Ji, P. Berry, D. M. Rotstein,
Bioorg. Med. Chem. Lett. 2010, 20, 4753–4756.
[14] I. P. J. Höglund, S. Silver, M. T. Engström, H. Salo, A.
Tauber, H. K. Kyyrönen, P. Saarenketo, A. M. Hoffrén,
K. Kokko, K. Pohjanoksa, J. Sallinen, J. M. Savola, S.
Wurster, O. A. Kallatsa, J. Med. Chem. 2006, 49, 6351–
6363.
[15] S. M. Roopan, R. Sompalle, Synth. Commun. 2016, 46,
645–672.
[16] For selected examples, see: a) D. R. Fandrick, D.
Reinhardt, J. N. Desrosiers, S. Sanyal, K. R. Fandrick, S.
Ma, N. Grinberg, H. Lee, J. J. Song, C. H. Senanayake,
Org. Lett. 2014, 16, 2834–2837; b) X. Q. Chu, W. Bin
Cao, X. P. Xu, S. J. Ji, J. Org. Chem. 2017, 82, 1145–
1154; c) H. B. Jalani, W. Cai, H. Lu, Adv. Synth. Catal.
2017, 359, 2509–2513. For selected examples on flow
synthesis of pyrimidines, see: d) A. J. E. Butler, M. J.
Thompson, P. J. Maydom, J. A. Newby, K. Guo, H.
Adams, B. Chen, J. Org. Chem. 2014, 79, 10196–10202;
e) M. Baumann, A. M. Rodriguez Garcia, I. R. Baxen-
dale, Org. Biomol. Chem. 2015, 13, 4231–4239.
[6] a) T. Kawabata, T. Mizugaki, K. Ebitani, K. Kaneda, J.
Am. Chem. Soc. 2003, 125, 10486–10487; b) R. Matsu-
zawa, S. Nishimura, K. Ebitani, ChemistrySelect 2017, 2,
10814–10817.
[7] Based on our homogeneous catalyst screening, NiCl2 was
found as optimal catalyst. From this investigation, we
selected water soluble hydrated NiCl2.6H2O as the Ni-
source to prepare heterogeneous Ni2+-mont.
[8] For reviews, see: a) R. Schlögl, Angew. Chem. Int. Ed.
2015, 54, 3465–3520; Angew. Chem. 2015, 127, 3531–
3589; b) M. Argyle, C. Bartholomew, Catalysts 2015, 5,
145–269. For selected references, see: c) J. W. Comer-
ford, J. H. Clark, D. J. MacQuarrie, S. W. Breeden,
Adv. Synth. Catal. 2019, 361, 1–7
6
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
��
These are not the final page numbers!