The Journal of Organic Chemistry
Page 14 of 16
Notes
Chloride Mediated Acetylations of Isosorbide: A Route to Powerful
Nitric Oxide Donor Furoxans. Org. Lett. 2018, 20, 3025-3029.
7) (a) Matsubara, R.; Kim, H.; Sakaguchi, T.; Xie, W.; Zhao, X.;
Nagoshi, Y.; Wang, C.; Tateiwa, M.; Ando, A.; Hayashi, M.;
Yamanaka, M.; Tsuneda, T., Modular Synthesis of Carbon-Substituted
Furoxans via Radical Addition Pathway. Useful Tool for
Transformation of Aliphatic Carboxylic Acids Based on "Build-and-
Scrap" Strategy. Org. Lett. 2020, 22, 1182-1187; (b) Matsubara, R.;
Ando, A.; Hayashi, M., Synthesis of cyanofuroxans from 4-
nitrofuroxans via CC bond forming reactions. Tetrahedron Lett. 2017,
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The authors declare no competing financial interest.
(
ACKNOWLEDGMENT
This work was financially supported by JSPS KAKENHI Grant
Numbers JP16K18844 and JP17J00025, Futaba Electronics
Memorial Foundation, Suzuken Memorial Foundation,
Inamori Foundation, and Daiichi Sankyo Foundation of Life
Science.
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8, 3337-3340; (c) Matsubara, R.; Eguchi, S.; Ando, A.; Hayashi, M.,
Synthesis of alkynyl furoxans. Rare carbon–carbon bond-forming
reaction on a furoxan ring. Org. Biomol. Chem. 2017, 15, 1965-1969.
(8) (a) Yerien, D. E.; Barata-Vallejo, S.; Postigo, A.,
Difluoromethylation Reactions of Organic Compounds. Chem. Eur. J.
2017, 23, 14676-14701; (b) Tomashenko, O. A.; Grushin, V. V.,
Aromatic Trifluoromethylation with Metal Complexes. Chem. Rev.
2011, 111, 4475-4521.
REFERENCES
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1
2
3
4
5
6
7
8
9
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1
2
3
4
5
6
7
8
9
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4
5
6
7
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(
1) Vitaku, E.; Smith, D. T.; Njardarson, J. T., Analysis of the
Structural Diversity, Substitution Patterns, and Frequency of Nitrogen
Heterocycles among U.S. FDA Approved Pharmaceuticals. J. Med.
Chem. 2014, 57, 10257-10274.
(2) Kekulé, A., Ueber die Constitution des Knallquecksilbers. Ann.
Chem. Pharm. 1857, 101, 200-213.
(9) (a) Zavarzina, O. V.; Rakitin, O. A.; Khmel’nitskii, L. I.,
Substitution of the Nitro Group in Chloronitrofuroxan by N- and O-
Trimethylsilyl Derivatives. Mendeleev Commun. 1994, 4, 135; (b)
Rakitin, O. A.; Godovikova, T. I.; Strelenko, Y. A.; Khmel'nitskii, L.
I., An unusual reaction of nitrochlorofuroxane with ammonia. Bull.
Acad. Sci. USSR, Div. Chem. Sci. 1986, 35, 2198-2198; (c) Calvino, R.;
Serafino, A.; Ferrarotti, B.; Gasco, A.; Sanfilippo, A., Syntheses,
Structures and Antimicrobial Properties of Some Halogenofuroxans
and Related Furazans. Arch. Pharm. 1984, 317, 695-701; (d) Calvino,
R.; Gasco, A.; Menziani, E.; Serafino, A., Unsymmetrically substituted
furoxans. VIII. Chloromethylfuroxans. J. Heterocycl. Chem. 1983, 20,
783-785; (e) Calvino, R.; Fruttero, R.; Gasco, A.; Mortarini, V.; Aime,
S., Unsymmetrically substituted furoxans. VII. A 13C NMR study of a
series of isomeric pairs of furoxans and the structure of the two
isomeric chloro-phenyl-furoxans. J. Heterocycl. Chem. 1982, 19, 427-
430; (f) Ungnade, H. E.; Kissinger, L. W., Nitration of
chloroglyoximes: Chlorofuroxans and other nitration products.
Tetrahedron 1963, 19, 143-154.
(
3) (a) Seymour, C. P.; Nakata, A.; Tsubaki, M.; Hayashi, M.;
Matsubara, R., A Fluorescent Naphthalenediimide-Alkoxyfuroxan
Photoinduced Nitric Oxide Donor. Bull. Chem. Soc. Jpn. 2019, 92, 162-
169; (b) Horton, A.; Nash, K.; Tackie-Yarboi, E.; Kostrevski, A.;
Novak, A.; Raghavan, A.; Tulsulkar, J.; Alhadidi, Q.; Wamer, N.;
Langenderfer, B.; Royster, K.; Ducharme, M.; Hagood, K.; Post, M.;
Shah, Z. A.; Schiefer, I. T., Furoxans (Oxadiazole-4N-oxides) with
Attenuated Reactivity are Neuroprotective, Cross the Blood Brain
Barrier, and Improve Passive Avoidance Memory. J. Med. Chem. 2018,
61, 4593-4607; (c) Seymour, C. P.; Tohda, R.; Tsubaki, M.; Hayashi,
M.; Matsubara, R., Photosensitization of Fluorofuroxans and Its
Application to the Development of Visible Light-Triggered Nitric
Oxide Donor. J. Org. Chem. 2017, 82, 9647-9654; (d) Matsubara, R.;
Takazawa, S.; Ando, A.; Hayashi, M.; Tohda, R.; Tsubaki, M., Study
on the Photoinduced Nitric-Oxide-Releasing Ability of 4-Alkoxy
Furoxans. Asian J. Org. Chem. 2017, 6, 619-626; (e) Ando, A.;
Matsubara, R.; Takazawa, S.; Shimada, T.; Hayashi, M.,
Fluorofuroxans: Synthesis and Application as Photoinduced Nitric
Oxide Donors. Asian J. Org. Chem. 2016, 5, 886-890; (f) Medana, C.;
Ermondi, G.; Fruttero, R.; Di Stilo, A.; Ferretti, C.; Gasco, A., Furoxans
as Nitric Oxide Donors. 4-Phenyl-3-furoxancarbonitrile: Thiol-
Mediated Nitric Oxide Release and Biological Evaluation. J. Med.
Chem. 1994, 37, 4412-4416; (g) Ghigo, D.; Calvino, R.; Heller, R.;
Calvino, R.; Alessio, P.; Fruttero, R.; Gasco, A.; Bosia, A.; Pescarmona,
G., Characterization of a new compound, S35b, as a guanylate cyclase
activator in human platelets. Biochem. Pharmacol. 1992, 43, 1281-
(10) Zavarzina, O. V.; Rakitin, O. A.; Khmel'nitskii, L. I., Nitro
group substitution in nitrochlorofuroxan using N- and O-trimethylsilyl
derivatives. Chem. Heterocycl. Compd. 1994, 30, 979-981.
(11) (a) Pasinszki, T.; Vass, G.; Klapstein, D.; Westwood, N. P. C.,
Generation, Spectroscopy, and Structure of Cyanoformyl Chloride and
Cyanoformyl Bromide, XC(O)CN. J. Phys. Chem. A 2012, 116, 3396-
3403; (b) Birckenbach, L.; Sennewald, K., 1. Zur Halogen-Einwirkung
auf Knallsäure und Knallate. —2. Trihalogen-nitroso-methane (XIX.
Mitteil. zur Kenntnis der Pseudohalogene). Ber. Dtsch. Chem. Ges. (A
and B Series) 1932, 65, 546-552; (c) Birckenbach, L.; Sennewald, K.,
Über Pseudohalogene. XV. Zur Reaktion der Knallsäure und ihrer
Salze mit Halogenen. Justus Liebigs Ann. Chem. 1931, 489, 7-30.
(12) Kekulé, A., Ueber die Constitution des Knallquecksilbers.
Justus Liebigs Ann. Chem. 1858, 105, 279-286.
1
288; (h) Feelisch, M.; Schönafingeri, K.; Noack, H., Thiol-mediated
generation of nitric oxide accounts for the vasodilator action of
furoxans. Biochem. Pharmacol. 1992, 44, 1149-1157; (i) Calvino, R.;
Fruttero, R.; Ghigo, D.; Bosia, A.; Pescarmona, G. P.; Gasco, A., 4-
Methyl-3-(arylsulfonyl)furoxans: a new class of potent inhibitors of
platelet aggregation. J. Med. Chem. 1992, 35, 3296-3300.
(13) Compound
1 was reported to be synthesized from
(
4) (a) Fershtat, L. L.; Makhova, N. N., Advances in the synthesis of
dichloroformaldoxime., Chen, W.; Zhang, J.; Wang, B.; Zhao, Z.;
Wang, X.; Hu, Y., Tandem Synthesis of 3-Chloro-4-iodoisoxazoles
from 1-Copper(I) Alkynes, Dichloroformaldoxime, and Molecular
Iodine. J. Org. Chem. 2015, 80, 2413-2417.
(14) The structures of compounds 2, 8b, 8f,11a, 15, 19b, 21b, 25a,
and 27c were determined by single-crystal X-ray diffraction analysis.
CCDC 1979369-1979377 contain the supplementary crystallographic
data for this paper. These data can be obtained free of charge from The
non-annelated polynuclear heterocyclic systems comprising the 1,2,5-
oxadiazole ring. Russ. Chem. Rev. 2016, 85, 1097-1145; (b) Makhova,
N. N.; Kulikov, A. S., Advances in the chemistry of monocyclic amino-
and nitrofuroxans. Russ. Chem. Rev. 2013, 82, 1007-1033; (c) Nikonov,
G.; Bobrov, S., 5.05
Heterocyclic Chemistry III, Katritzky, A. R.; Ramsden, C. A.; Scriven,
E. F. V.; Taylor, R. J. K., Eds. Elsevier: Oxford, 2008; Vol. 5, pp 315-
- 1,2,5-Oxadiazoles. In Comprehensive
3
95; (d) Paton, R. M., Product Class 7: 1,2,5-Oxadiazoles. In Sience of
Cambridge
Crystallographic
Data
Centre
via
Synthesis, 2004 ed.; Storr, R. C.; Gilchrist, T. L., Eds. Georg Thieme
Verlag: Stuttgart, 2004; Vol. 13, pp 185-218; (e) Sheremetev, A. B.;
Makhova, N. N.; Friedrichsen, W., Monocyclic furazans and furoxans.
In Adv. Heterocycl. Chem., Academic Press: 2001; Vol. 78, pp 65-188.
http://www.ccdc.cam.ac.uk/data_request/cif.
(15) Del Grosso, E.; Boschi, D.; Lazzarato, L.; Cena, C.; Di Stilo,
A.; Fruttero, R.; Moro, S.; Gasco, A., The Furoxan System: Design of
Selective Nitric Oxide (NO) Donor Inhibitors of COX-2 Endowed with
Anti-Aggregatory and Vasodilating Activities. Chem. Biodivers. 2005,
2, 886-900.
(16) Mallory, F. B.; Cammarata, A., Evidence for the Transient
Existence of 1,2-Dinitrosoalkenes. J. Am. Chem. Soc. 1966, 88, 61-64.
(17) (a) Cui, L.; Chen, H.; Liu, C.; Li, C., Silver-Catalyzed
Decarboxylative Allylation of Aliphatic Carboxylic Acids in Aqueous
Solution. Org. Lett. 2016, 18, 2188-2191; (b) Liu, X.; Wang, Z.; Cheng,
(
5) Very recently diacylfuroxans were reported to have GPX4
inhibitory activities., Eaton, J. K.; Ruberto, R. A.; Kramm, A.;
Viswanathan, V. S.; Schreiber, S. L., Diacylfuroxans Are Masked
Nitrile Oxides That Inhibit GPX4 Covalently. J. Am. Chem. Soc. 2019,
1
41, 20407-20415.
6) Kielty, P.; Smith, D. A.; Cannon, P.; Carty, M. P.; Kennedy, M.;
McArdle, P.; Singer, R. J.; Aldabbagh, F., Selective Methylmagnesium
(
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