3-AMINOPYRAZINO-2-HYDROXAMIC ACID synthesis
- Product Name:3-AMINOPYRAZINO-2-HYDROXAMIC ACID
- CAS Number:24719-09-3
- Molecular formula:C5H6N4O2
- Molecular Weight:154.13
6761-52-0
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59046-72-9
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24719-09-3
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37993-76-3
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$187.46/1g
Yield:37993-76-3 91% ,24719-09-3 52%
Reaction Conditions:
with iodine in dimethyl sulfoxide at 100;Catalytic behavior;Temperature;Solvent;
Steps:
1 General procedure for the syntheses of 2-arylisoquinoline derivatives 4
General procedure: General procedure for the syntheses of 2-arylisoquinoline derivatives 4 3-Aminopyrazine-2-carbohydrazide (1, 77mg, 0.5mmol) 2-(arylethynyl) benzaldehydes 2 (0.5mmol), iodine (13mg, 0.05mmol), and DMSO (5.0mL) was added into a dry 25mL flask. The reaction mixture was stirred at 100°C for 4-10h until all the 1 and intermediate product hydrazone were consumed which was monitored by TLC.
The separation and purification of the products 4 were the same to those of 3. In the process of 4a, the filtrate was extracted with ethyl acetate (30mL*3). The organic layer was combined and dried by anhydrous Na2SO4. The ethyl acetate was recovered by rotary evaporation, and the residue was purified by column chromatography using ethyl acetate and petroleum ether (2:1) as an eluant to give 3-amino-N-hydroxypyrazine-2-carboxamide (8) in 52% yield. 4.2.1 3-Phenylisoquinoline (4a) M.p. 104-105°C (Lit.20 103-104°C); 1H NMR (CDCl3, 400MHz): δH 7.39-7.44 (m, 1H, ArH), 7.49-7.59 (m, 3H, ArH), 7.66-7.70 (m, 1H, ArH), 7.86 (d, J=8.0Hz, 1H, ArH), 7.98 (d, J=8.4Hz, 1H, ArH), 8.06 (s, 1H, ArH), 8.11-8.14 (m, 2H, ArH), 9.33 (s, 1H, ArH). 13C NMR (CDCl3, 100MHz): δC 116.5, 126.9, 127.0, 127.1, 127.6, 127.8, 128.5, 128.8, 130.5, 136.7, 139.6, 151.3, 152.4. IR (KBr): ν 2912, 1625, 1585, 1562, 1515, 1489, 1332, 1279, 1196, 1139, 1131, 1035, 960, 944, 884, 742, 713, 680cm-1. HRMS (APCI, m/z): Calcd for C15H12N [M+ H]+ 206.0964, found 206.0973. 4.2.2 3-Amino-N-hydroxypyrazine-2-carboxamide (8) M.p. 198-200°C (Lit.21 196°C), 1H NMR (DMSO-d6, 400MHz): δH 7.42 (brs, 3H, NH2+OH), 7.76 (d, J=2.4Hz, 1H, ArH), 8.17 (d, J=2.4Hz, 1H, ArH), 9.43 (brs, 1H, NH). 13C NMR (DMSO-d6, 100MHz): δC 126.3, 131.3, 146.8, 155.1, 163.6.
References:
Pan, Wan-Chen;Liu, Jian-Quan;Wang, Xiang-Shan [Tetrahedron,2018,p. 1468 - 1475]
16298-03-6
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24719-09-3
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