Organic Letters
Letter
‡
(14) Tomilov, Yu. V.; Platonov, D. N.; Dorokhov, D. V.; Zhalnina, A.
A. Russ. Chem. Bull. 2008, 57, 1252.
(15) Moisan, L.; Odermatt, S.; Gombosuren, N.; Carella, A.; Rebek,
low ΔHr = 6−12 kcal/mol, EA = 2.4−8 kcal/mol [B3LYP/6-
311+G(d,p) and semiempirical PM6].25
In summary, a novel effective approach to the synthesis of
pyridazines by the two-stage procedure from ketones was
described. The approach employs simple reactions comprising
(1) Vilsmeier−Haack reaction of enolizable ketone leading to
chlorovinyl aldehydes and (2) imination of the former with
oxamic acid thiohydrazides and cascade electrocyclization/
aromatization of the resulting 2,3-diazatriene affording highly
substituted pyridazines in moderate to excellent isolated yields
(32−89%). Starting materials are readily available, and
functional group tolerance is quite good. The ease of 2,3-
diazahexatriene system construction and the broad availability
of reagents imply that an extensive range of substituents can be
selectively incorporated in the pyridazine ring. The full
potential of this methodology and an exploration of a greater
variety of substituents must await additional studies.
J. Eur. J. Org. Chem. 2008, 2008, 1673.
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(17) (a) Trost, B. M.; Biannic, B. Org. Lett. 2015, 17, 1433.
(18) Landreau, C.; Deniaud, D.; Reliquet, A.; Reliquet, F.; Meslin, J.
J. Heterocycl. Chem. 2001, 38, 93.
(19) Milevsky, B. G.; Soloveva, N. P.; Chibisova, T. A.; Yarovenko, V.
́
N.; Zayakin, E. S.; Chernyshev, V. V.; Krayushkin, M. M.; Traven, V. F.
Russ. Chem. Bull. 2012, 61, 2311.
(20) Lednicer, D. Steroid Chemistry at a Glance; John Wiley & Sons
Ltd.: 2011; p 144.
(21) Amr, A. E.; Abdulla, M. M. Bioorg. Med. Chem. 2006, 14, 4341.
(22) Gogoi, S.; Shekarrao, K.; Duarah, A.; Bora, T. C.; Gogoi, S.;
Boruah, R. C. Steroids 2012, 77, 1438.
ASSOCIATED CONTENT
■
(23) Zhang, B.; Song, L.; Li, Y.; Li, Y.; Guo, Y.; Zhang, E.; Liu, H.
S
* Supporting Information
Detailed experimental procedures, spectral data for all products,
and the X-ray data for 10b (CIF). The Supporting Information
(24) (a) Zhang, B.; Zhang, E.; Pang, L.; Song, L.; Li, Y.; Yu, B.; Liu,
(25) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.;
Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci,
B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H.
P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.;
Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima,
T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.;
Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin,
K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.;
Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.;
Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.;
Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.;
Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.;
Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador,
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
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