* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
General procedure: N,N-Dimethylformamide (0.5 mg, 0.0673 mmol) was added dropwise to a slurry of 2,3-dihydroxyquinoxaline (2.0 g,12.3 mmol) and thionyl chloride (2.92 g, 24.6 mmol) in1-chlorobutane (20 mL). The mixture was refluxed for 1h.Then cooled to ambient temperature, the obtained needles were filtered, washed with ethyl ether, and dried.
Reference:
[1] Revue Roumaine de Chimie, 2017, vol. 62, # 12, p. 903 - 906
[2] Journal of Heterocyclic Chemistry, 2009, vol. 46, # 2, p. 317 - 319
[3] Pesticide Science, 1995, vol. 43, # 4, p. 263 - 266
[4] Monatshefte fur Chemie, 2010, vol. 141, # 10, p. 1145 - 1151
[5] Journal of Molecular Structure, 2017, vol. 1139, p. 238 - 246
[6] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 7, p. 1809 - 1814
2
[ 6309-61-1 ]
[ 39267-05-5 ]
Reference:
[1] Helvetica Chimica Acta, 1994, vol. 77, # 6, p. 1549 - 1556
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1110 - 1112
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 20, p. 6433 - 6441
[4] Journal of the Chemical Society, 1949, p. 1271,1275
[5] Journal of the Chemical Society, 1953, p. 2816,2819
[6] Chemische Berichte, 1883, vol. 16, p. 1532[7] Justus Liebigs Annalen der Chemie, 1887, vol. 237, p. 350
[8] Molecules, 2004, vol. 9, # 4, p. 223 - 231
3
[ 496-72-0 ]
[ 39267-05-5 ]
Reference:
[1] Helvetica Chimica Acta, 1994, vol. 77, # 6, p. 1549 - 1556
[2] Monatshefte fur Chemie, 2010, vol. 141, # 10, p. 1145 - 1151
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 20, p. 6433 - 6441
[4] Revue Roumaine de Chimie, 2017, vol. 62, # 12, p. 903 - 906
[5] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 7, p. 1809 - 1814
4
[ 6309-61-1 ]
[ 10026-13-8 ]
[ 39267-05-5 ]
Reference:
[1] Chemische Berichte, 1883, vol. 16, p. 1532[2] Justus Liebigs Annalen der Chemie, 1887, vol. 237, p. 350
disodium-Z-1,2-dicyano-1,2-ethylenedithiolate[ No CAS ]
7-methyl-1,4-dithiino[2,3-b]quinoxaline-2,3-dicarbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
EXAMPLE 4 Preparation of 7-Methyl-1,4-dithiino-(2,3-b)quinoxaline-2,3-dicarbonitrile The process of Example 1 is followed except that the 2,3-dichloro-6-nitroquinoxaline is replaced by 3.0 g of <strong>[39267-05-5]2,3-dichloro-6-methylquinoxaline</strong> and 3.3 g of the disodium-Z-1,2-dicyano-1,2-ethylenedithiolate is used. The recovered material is an orange powder weighing 3.52 g with a calculated overall yield of 88 percent and has a melting point of 213 to 215 C.
EXAMPLE 15 Preparation of 6-Methyl-1,3-dithiolo-(4,5-b)-quinoxaline-2-ylidene-propanedinitrile The process of Example 13 is followed except that the 2,3-dichloro-6-nitroquinoxaline is replaced by 3.0 g of <strong>[39267-05-5]2,3-dichloro-6-methylquinoxaline</strong> and 3.84 g of the di(potassiomercapto)methylenemalononitrile is used. The recovered material is a yellow powder weighing 2.9 g with a calculated overall yield of 73 percent and has a melting point of 265 to 267 C.
1,2,3,4,4a,5-hexahydro-10-methylpyrido[1',2':4,5][1,4]oxazino[2,3-b]quinoxaline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 18 1,2,3,4,4a,5-Hexahydro-9-methylpyrido[1',2':4,5][1,4]oxazino[2,3-b]quinoxaline and 1,2,3,4,4a,5-hexahydro-10-methylpyrido[1',2':4,5][1,4]oxazino[2,3-b]quinoxaline If <strong>[39267-05-5]2,3-dichloro-6-methylquinoxaline</strong> is treated with 2-piperidinomethanol as described in Example 2, the above compounds are obtained.
N‐[(3‐aminophenyl)methyl]‐3‐chloro‐7‐methylquinoxalin‐2‐amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In ethanol; at 120℃; for 6h;
2 mmol of 2,3-dichloro-7-methylquinoxaline (purchase),2.2 mmol of 3-aminobenzylamine and 2.4 mmol of triethylamine were added to the isopropanol solution,The mixture was refluxed at 120°C for 6h.After the reaction is completed, flash silica gel column chromatography (petroleum ether:ethyl acetate=2:1),Purified N-(3-aminobenzyl)-2-amine-3-chloro-7-methylquinoxaline;