CN107573351A - A kind of method for synthesizing nitrogen-containing heterocycle compound - Google Patents

A kind of method for synthesizing nitrogen-containing heterocycle compound Download PDF

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CN107573351A
CN107573351A CN201711062679.7A CN201711062679A CN107573351A CN 107573351 A CN107573351 A CN 107573351A CN 201711062679 A CN201711062679 A CN 201711062679A CN 107573351 A CN107573351 A CN 107573351A
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nitrogen
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containing compound
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phenyl
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吴建伟
徐迈
鲍霞
魏亦军
王凤武
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Huainan Normal University
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Huainan Normal University
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Abstract

The invention discloses a kind of method for synthesizing nitrogen-containing heterocycle compound, this method carries out cascade reaction as initiation material using pyrrole aldehyde, halides and amidine in alkaline environment and builds nitrogen-containing heterocycle compound, this method reaction intermediate is without separation, it is simple to operate, yield is higher, without metallic catalyst in reaction, there is the characteristics of efficient, inexpensive, industrially prepared for nitrogen-containing heterocycle compound has higher practical value.

Description

A kind of method for synthesizing nitrogen-containing heterocycle compound
Technical field
The present invention relates to organic synthesis field, specially a kind of method for synthesizing nitrogen-containing heterocycle compound.
Background technology
The especially nitrogenous heterocyclic compound of heterocycle compound occupies very big ratio in the medicine of commercialization, and big Nitrogen heterocyclic ring is that it possesses the key structure factor of bioactivity in most medicines.Pyrroles's pyrazine is a kind of important azabicyclo Construction unit, it is widely present in natural products and synthetic drug.Pyrroles's pyrazine and its derivative are in medicine and chemical intermediate Aspect shows more and more important value, and at present prepared by the following several method of the compound generally use：(1) using gloomy field- Belize-Harry Hillman reaction (Morita-Baylis-Hillman reaction) and Ku Ertisi rearrangement reactions (Curtius Reaction) four steps synthesis (Tetrahedron 2011,67,7563)；(2) gold catalysis propargyl nitrogen-containing heterocycle compound point Sub- intramolecular cyclization (J.Am.Chem.Soc.2006,128,12050)；(3) intermediate obtained using N- alkylated reactions is again in vinegar The sour lower cyclodehydration synthesis (Tetrahedron 2014,70,7534) of ammonium effect；(4) it is more using pyrrole aldehyde and alkene nitrine Minot reaction synthesis (Org.Lett.2010,12,3863)；(5) it is condensed by pyrrole aldehyde and aminoacetal, strong acid catalyst Cyclic (J.Am.Chem.Soc. 1955,77,6355).
The general route of above-mentioned synthetic method is longer, and substrate spectrum is narrow, and harsh reaction condition, yield is relatively low, or needs high Expensive metallic catalyst etc..Therefore develop efficiently and inexpensive new synthetic method has necessity.
The content of the invention
It is an object of the invention to provide a kind of method for synthesizing nitrogen-containing heterocycle compound, to solve to propose in above-mentioned background technology Efficient and inexpensive synthetic method the problem of.
To achieve the above object, the present invention provides following technical scheme：A kind of synthetic method of nitrogen-containing heterocycle compound, with pyrroles Formaldehyde, halides and amidine are initiation material, add a kind of alkali, and heating in organic solvent obtains the nitrogen heterocyclic ring shown in formula (I) Compound；
Wherein：
R1 is selected from C1-C10 alkyl, naphthyl or phenyl, and wherein phenyl has the 0-3 substituents being selected from the group：Methyl, methoxy Base, halogen, phenyl, mesyl；
R2 is selected from H or C1-C10 alkyl.
Preferably, described halides are 1- halo -2- alkyl ketones, 2- haloacetyls naphthalene or 2- halo acetophenones, wherein benzene Base has the 0-3 substituents being selected from the group：Methyl, methoxyl group, halogen, phenyl, mesyl.
Preferably, described amidine is carbonamidine, ethanamidine or C3-C10 acid amidines and its acetic acid, hydrochloride.
Preferably, described alkali be cesium carbonate, potassium carbonate, sodium carbonate, sodium hydroxide, triethylamine, 1,8- diazabicyclos [5, 4,0] one or more in 11 carbon -7- alkene (DBU), preferably potassium carbonate.
Preferably, described organic solvent is in ethanol, dichloromethane, acetonitrile, DMF (DMF), toluene One or more, preferably DMF (DMF).
Preferably, the trip temperature that enters of described cascade reaction is 30-100 DEG C, preferably 50 DEG C.
Preferably, the time of described cascade reaction is 1-24h, preferably 12h.
Preferably, the pyrrole aldehyde, halides, amidine, the mol ratio of alkali are：1:1.1:1.5:4.
Preferably, the nitrogen-containing heterocycle compound includes following synthesis step：S1：Pyrrole aldehyde, halo are added in the reactor Thing, alkali and organic solvent, heating response is for a period of time；S2：Amidine and alkali are added into above-mentioned S1 reaction systems, continues heating response Stop heating after a period of time；S3, water, ethyl acetate extraction are added into above-mentioned S2 reaction systems, saturated nacl aqueous solution is washed Wash, wash, merge organic phase, anhydrous sodium sulfate drying, revolving removes solvent, residue silica gel column chromatogram separating purification, oil Ether/ethyl acetate obtains solid as eluant, eluent.
Compared with prior art, the beneficial effects of the invention are as follows：The method of the synthesis nitrogen-containing heterocycle compound, in alkaline environment Cascade reaction is carried out as initiation material using pyrrole aldehyde, halides and amidine and builds nitrogen-containing heterocycle compound, this method reaction is middle Body is without separation, and simple to operate, yield is higher, and without metallic catalyst in reaction, the industry for nitrogen-containing heterocycle compound is made It is standby that there is higher practical value.
Embodiment
The technical scheme in the embodiment of the present invention is clearly and completely described below, it is clear that described embodiment is only It is part of the embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, ordinary skill people The every other embodiment that member is obtained under the premise of creative work is not made, belongs to the scope of protection of the invention.
Embodiment 1
2- pyrrole aldehydes 1 (1mmol), bromoacetophenone (1.1mmol) and potassium carbonate are added in 50mL round-bottomed flask (2mmol), anhydrous DMF 10mL being added, reaction is heated to 50 DEG C, after reacting 30 minutes, reaction raw materials 1,2 Fundamental reaction is complete, and formamidine acetate (1.5mmol) is added directly into reaction system, potassium carbonate (2mmol) is added, continues 50 Reacted 12 hours at DEG C, stop heating, water terminating reaction, ethyl acetate extraction, saturated sodium-chloride are added into reactant mixture Solution washs, washing, merges organic phase, anhydrous sodium sulfate drying, and revolving removes solvent, and residue is separated pure with silica gel column chromatography Change, petrol ether/ethyl acetate obtains yellow solid, yield 86% as eluant, eluent.
Nuclear magnetic resonance：1H NMR(500MHz,CDCl3/TMS)δ8.95(s,1H),8.93-8.92 (m,1H),8.11(s,1H), 7.82-7.81 (m, 2H), 7.65-7.62 (m, 1H), 7.55-7.52 (m, 2H), 7.09 (d, J=2.0Hz, 2H)；13C NMR (125MHz,CDCl3/TMS)δ190.9, 147.9,139.0,137.8,132.9,130.1,129.6,128.6,124.5, 119.7,117.2, 107.5。
Embodiment 2
Using method same as Example 1, yellow solid, yield 80% are obtained instead of formamidine acetate with ethenylamidine hydrochloride.
Nuclear magnetic resonance：1H NMR(500MHz,CDCl3/TMS)δ8.84(s,1H),7.89-7.88 (m,2H),7.68-7.65 (m, 1H), 7.53-7.50 (m, 2H), 7.29-7.27 (m, 1H), 6.88 (dd, J=1.0,4.0Hz, 1H), 6.82 (dd, J= 2.0,4.5Hz,1H),2.28(s, 3H)；13C NMR(100MHz,CDCl3/TMS)δ191.9,145.2,136.3,135.3, 134.6, 129.4,129.3,128.0,127.6,123.2,115.4,104.7,20.9.
Embodiment 3
Using method same as Example 1, yellow solid, yield are obtained instead of 2- bromoacetophenones with the bromo- 4'- bromoacetophenones of 2- 91%.
Nuclear magnetic resonance：1H NMR(500MHz,CDCl3/TMS)δ8.95(s,1H),8.93-8.89 (m,1H),8.09(s,1H), 7.71-7.67(m,4H),7.12-7.10(m,2H)；13C NMR(125MHz,CDCl3/TMS)δ189.6,148.1,139.0, 136.5,131.9,131.1, 130.1,127.6,124.3,119.7,117.3,107.7。
Embodiment 4
Using method same as Example 1,2- bromoacetophenones are replaced with the bromo- 4'- bromoacetophenones of 2-, vinegar is replaced with ethenylamidine hydrochloride Sour carbonamidine obtains yellow solid, yield 84%.
Nuclear magnetic resonance：1H NMR(400MHz,CDCl3/ TMS) δ 8.83 (s, 1H), 7.73 (d, J=8.8Hz, 2H), 7.65 (d, J=8.8Hz, 2H), 7.28-7.27 (m, 1H), 6.88 (dd, J=1.2Hz, 4.4Hz, 1H), 6.82 (dd, J=2.4Hz, 4.4Hz,1H),2.27 (s,3H)；13C NMR(100MHz,CDCl3/TMS)δ190.8,145.5,135.7,135.2, 132.7,130.8,130.1,128.0,122.7,115.5,115.4,114.9,21.1。
Embodiment 5
Using method same as Example 1, yellow solid is obtained instead of 2- bromoacetophenones with the bromo- 4'- methoxyacetophenones of 2-, Yield 82%.
Nuclear magnetic resonance：1H NMR(500MHz,CDCl3/TMS)δ8.93(s,1H),8.76-8.75 (m,1H),8.05(s,1H), 7.86 (d, J=9.0Hz, 2H), 7.06 (d, J=1.5 Hz, 2H), 7.02 (d, J=9.0Hz, 2H), 3.92 (s, 3H)；13C NMR(125MHz, CDCl3/TMS)δ189.3,163.5,147.6,137.3,132.1,130.1,129.9,124.8, 119.0,116.8,113.9,106.9,55.5。
Embodiment 6
Using method same as Example 1,2- bromoacetophenones are replaced with the bromo- 4'- methoxyacetophenones of 2-, with ethenylamidine hydrochloride generation Yellow solid, yield 75% are obtained for formamidine acetate.
Nuclear magnetic resonance：1H NMR(400MHz,CDCl3/ TMS) δ 8.83 (s, 1H), 7.86 (d, J=8.8Hz, 2H), 7.24- 7.23 (m, 1H), 7.96 (d, J=8.8Hz, 2H), 6.87 (dd, J=0.8Hz, 4.0Hz, 1H), 6.81 (dd, J=2.4Hz, 4.0Hz,1H),3.89 (s,3H),2.30(s,3H)；13C NMR(100MHz,CDCl3/TMS)δ190.1,165.0, 144.8, 134.0,132.1,128.9,127.9,123.5,115.4,115.2,114.6,104.6, 55.6,20.5。
Embodiment 7
Using method same as Example 1, yellow solid is obtained instead of 2- bromoacetophenones with the bromo- 4'- methyl acetophenones of 2-, produced Rate 83%.
Nuclear magnetic resonance：1H NMR(500MHz,CDCl3/TMS)δ8.94(s,1H),8.86-8.85 (m,1H),8.09(s,1H), 7.74 (d, J=7.5Hz, 2H), 7.34 (d, J=7.5 Hz, 2H), 7.08 (d, J=2.0Hz, 2H), 2.47 (s, 3H)；13C NMR(100MHz, CDCl3/TMS)δ190.5,147.8,143.5,138.3,135.1,130.1,129.8,129.3, 124.7,119.3,116.9,107.1,21.6。
Embodiment 8
Using method same as Example 1,2- bromoacetophenones are replaced with the bromo- 4'- methyl acetophenones of 2-, replaced with ethenylamidine hydrochloride Formamidine acetate obtains yellow solid, yield 79%.
Nuclear magnetic resonance：1H NMR(400MHz,CDCl3/ TMS) δ 8.83 (s, 1H), 7.78 (d, J=8.0Hz, 2H), 7.29 (d, J=8.0Hz, 2H), 7.26-7.25 (m, 1H), 6.86 (dd, J=1.2Hz, 4.4Hz, 1H), 6.80 (dd, J=2.4Hz, 4.4Hz,1H),2.44 (s,3H),2.28(s,3H)；13C NMR(100MHz,CDCl3/TMS)δ191.4,146.0, 145.1, 134.8,133.7,130.0,129.7,127.9,123.4,115.3,115.2,104.4, 21.8,20.7。
Embodiment 9
Using method same as Example 1, yellow liquid, yield 64% are obtained instead of 2- bromoacetophenones with the bromo- 2- butanone of 1-.
Nuclear magnetic resonance：1H NMR(400MHz,CDCl3/ TMS) δ 9.13 (t, J=2.0Hz, 1H), 8.94 (s, 1H), 8.49 (s, 1H), 7.07 (d, J=2.0Hz, 2H), 3.10 (q, J=7.2Hz, 2H), 1.31 (t, J=7.2Hz, 3H)；13C NMR (100MHz,CDCl3/TMS) δ195.8,147.6,135.3,120.6,117.6,107.6,100.0,31.6,8.6。
Embodiment 10
Using method same as Example 1,2- bromoacetophenones are replaced with the bromo- 2- butanone of 1-, tumer is replaced with ethenylamidine hydrochloride Amidine obtains yellow liquid, yield 55%.
Nuclear magnetic resonance：1H NMR(400MHz,CDCl3/ TMS) δ 9.73 (s, 1H), 7.46 (dd, J=4.0Hz, J=2.0Hz, 1H), 6.83 (t, J=2.0Hz, 1H), 6.31 (dd, J=4.0,2.0Hz, 1H), 2.52 (s, 3H), 2.44 (q, J=7.2Hz, 2H), 1.07 (t, J=7.2Hz, 3H)；13C NMR(100MHz,CDCl3/TMS)δ190.8,146.7,129.3, 120.2, 113.6,113.1,105.6,100.0,30.5,16.7,8.6。
Embodiment 11
Using method same as Example 1, yellow solid is obtained instead of 2- bromoacetophenones with the bromo- 4'- first sulfo group acetophenones of 2-, Yield 74%.
Nuclear magnetic resonance：1H NMR(400MHz,CDCl3/ TMS) δ 9.03 (s, 1H), 8.97 (s, 1 H), 8.13 (d, J=8.4Hz, 2H), 8.07 (s, 1H), 7.96 (d, J=8.4Hz, 2 H), 7.17-7.14 (m, 2H), 3.14 (s, 3H)；13C NMR(100MHz, CDCl3/TMS)δ 189.2,148.4,143.7,142.6,140.2,130.2,127.7,127.4,124.1,120.4, 117.9,108.5,44.4。
Embodiment 12
Using method same as Example 1,2- bromoacetophenones are replaced with the bromo- 4'- first sulfo group acetophenones of 2-, with ethenylamidine hydrochloride generation Yellow solid, yield 70% are obtained for formamidine acetate.
Nuclear magnetic resonance：1H NMR(400MHz,CDCl3/ TMS) δ 8.87 (s, 1H), 8.09 (d, J=8.4Hz, 2H), 8.04 (d, J=8.4Hz, 2H), 7.39 (s, 1H), 6.94 (d, J=3.6Hz, 1H), 6.87-6.85 (m, 1H), 3.11 (s, 3H), 2.27 (s,3H)；13C NMR(100MHz,CDCl3/TMS)δ190.5,145.9,145.3,140.8,137.1,130.2, 128.4, 128.1,122.4,116.1,116.0,105.8,44.2,21.4。
Embodiment 13
Using method same as Example 1, yellow solid is obtained instead of 2- bromoacetophenones with the bromo- 4'- phenyl acetophenones of 2-, produced Rate 78%.
Nuclear magnetic resonance：1H NMR(400MHz,CDCl3)δ8.95(s,1H),8.91(m,1H), 8.17(s,1H),7.91(d,J =8.8Hz, 2H), 7.75 (d, J=8.8Hz, 2H), 7.67-7.65 (m, 2H), 7.51-7.40 (m, 3H), 7.09 (d, J= 2.0Hz,2H).13C NMR(100MHz, CDCl3)δ190.3,147.9,145.5,139.7,138.6,136.4,130.3, 130.1,129.0, 128.3,127.3,127.2,124.7,119.5,117.1,107.4。
Embodiment 14
Using method same as Example 1,2- bromoacetophenones are replaced with the bromo- 4'- phenyl acetophenones of 2-, replaced with ethenylamidine hydrochloride Formamidine acetate obtains yellow solid, yield 73%.
1H NMR(400MHz,CDCl3/ TMS) δ 8.85 (s, 1H), 7.95 (d, J=8.4Hz, 2H), 7.71 (d, J= 8.4Hz, 2H), 7.64-7.62 (m, 2H), 7.50-7.39 (m, 3H), 7.32-7.31 (m, 1H), 6.88 (dd, J=4.4, 1.2Hz, 1H), 6.82 (dd, J=4.4,2.4Hz, 1H), 2.32 (s, 3H)；13C NMR(100MHz,CDCl3/TMS) δ 191.3,147.5,145.1,139.4,135.0,134.9,130.1,129.0,128.6,128.0, 127.9,127.3, 123.3,115.5,115.4,104.7,20.9。
Embodiment 15
Using method same as Example 1, yellow solid, yield are obtained instead of 2- bromoacetophenones with 2- acetyl bromides naphthalene 81%.
Nuclear magnetic resonance：1H NMR(400MHz,CDCl3)δ8.96(s,1H),8.92-8.91(m, 1H),8.31(s,1H),8.18 (s, 1H), 7.99-7.90 (m, 4H), 7.65-7.55 (m, 2H), 7.10 (d, J=1.6Hz, 2H)13C NMR(100MHz, CDCl3/TMS)δ190.6,147.8, 138.7,135.3,134.9,132.2,131.2,130.1,129.3,128.7, 128.5,127.9, 127.1,125.4,124.8,119.6,117.2,107.5。
Embodiment 16
Using method same as Example 1,2- bromoacetophenones are replaced with 2- acetyl bromides naphthalene, tumer is replaced with ethenylamidine hydrochloride Amidine obtains yellow solid, yield 70%.
Nuclear magnetic resonance：1H NMR(400MHz,CDCl3)δ8.90(s,1H),8.32(s,1H), 8.03-7.86(m,4H), (7.66-7.62 m, 1H), 7.57-7.53 (m, 1H), 7.33-7.32 (m, 1H), 6.92 (dd, J=4.0,0.8Hz, 1H), 6.82 (dd, J=4.0,2.4Hz, 1H), 2.31 (s, 3H)13C NMR(100MHz,CDCl3/TMS)δ191.6,144.9, 143.0,136.4, 134.8,133.6,132.7,132.2,129.8,129.4,128.0,128.7,127.9,127.2, 124.0,123.4,120.0,115.7,105.2,20.6。
Embodiment 17
Using method same as Example 1, yellow solid is obtained instead of 2- bromoacetophenones with the bromo- 2'- methoxyacetophenones of 2-, Yield 69%.
Nuclear magnetic resonance：1H NMR(400MHz,CDCl3) δ 9.18 (t, J=1.6Hz, 1H), 8.94 (s, 1H), 8.02 (s, 1H), 7.51 (ddd, J=8.4,7.6,1.6Hz, 1H), 7.39 (dd, J=7.6,1.6Hz, 1H), 7.12-7.06 (m, 3H), 7.02 (d, J=8.4Hz, 1H), 3.77 (s, 3H)13C NMR(100MHz,CDCl3/TMS)δ189.8,156.1,146.8,139.0, 131.1, 129.3,128.4,126.7,124.2,119.5,119.2,116.4,110.4,106.5,54.6。
Embodiment 18
Using method same as Example 1,2- bromoacetophenones are replaced with the bromo- 2'- methoxyacetophenones of 2-, with ethenylamidine hydrochloride generation Yellow solid, yield 62% are obtained for formamidine acetate.
Nuclear magnetic resonance：1H NMR(400MHz,CDCl3) δ 8.77 (s, 1H), 7.76 (dd, J=7.6,2.0Hz, 1H), 7.55 (ddd, J=8.4,7.6,2.0Hz, 1H), 7.46-7.45 (m, 1H), 7.08 (td, J=7.6,0.8Hz, 1H), 6.93 (d, J =8.4Hz, 1H), 6.84 (dd, J=4.0,1.2Hz, 1H), 6.79 (dd, J=4.0,2.4Hz, 1H), 3.53 (s, 3H), 2.30(s,3H).13C NMR(100MHz,CDCl3/TMS)δ190.5,159.2,144.8, 135.8,135.0,131.1, 128.3,127.5,126.0,121.3,115.1,115.1,112.1, 104.4,55.5,20.8。
All it is incorporated as referring in this application in all documents that the present invention refers to, is individually recited just as each document As with reference to such.In addition, it is to be understood that after the above of the present invention has been read, those skilled in the art can be to this hair Bright to make various changes or modifications, these equivalent form of values equally fall within letter of authorization limited range appended by the application.

Claims (9)

  1. A kind of 1. method for synthesizing the nitrogen-containing heterocycle compound shown in formula (I), it is characterised in that with pyrrole aldehyde, halides and amidine For initiation material, a kind of alkali is added, heating in organic solvent obtains the nitrogen-containing heterocycle compound shown in formula (I)；
    Wherein：
    R1 is selected from C1-C10 alkyl, naphthyl or phenyl, and wherein phenyl has the 0-3 substituents being selected from the group：Methyl, methoxy Base, halogen, phenyl, mesyl；
    R2 is selected from H or C1-C10 alkyl.
  2. A kind of 2. method for synthesizing nitrogen-containing compound according to claim 1, it is characterised in that：Described halides are 1- Halo -2- alkyl ketones, 2- haloacetyls naphthalene or 2- halo acetophenones, wherein phenyl have the 0-3 substituents being selected from the group： Methyl, methoxyl group, halogen, phenyl, mesyl.
  3. A kind of 3. method for synthesizing nitrogen-containing compound according to claim 1, it is characterised in that：Described amidine be carbonamidine, Ethanamidine or C3-C10 acid amidines and its acetic acid, hydrochloride.
  4. A kind of 4. method for synthesizing nitrogen-containing compound according to claim 1, it is characterised in that：Described alkali is carbonic acid One in caesium, potassium carbonate, sodium carbonate, sodium hydroxide, triethylamine, the carbon -7- alkene (DBU) of 1,8- diazabicyclos [5,4,0] 11 Kind is a variety of, preferably potassium carbonate.
  5. A kind of 5. method for synthesizing nitrogen-containing compound according to claim 1, it is characterised in that：Described organic solvent is One or more in ethanol, dichloromethane, acetonitrile, DMF (DMF), toluene, preferably N, N- dimethyl Formamide (DMF).
  6. A kind of 6. method for synthesizing nitrogen-containing compound according to claim 1, it is characterised in that：Described cascade reaction It is 30-100 DEG C to enter trip temperature, preferably 50 DEG C.
  7. A kind of 7. method for synthesizing nitrogen-containing compound according to claim 1, it is characterised in that：Described cascade reaction Time is 1-24h, preferably 12h.
  8. A kind of 8. method for synthesizing nitrogen-containing compound according to claim 1, it is characterised in that：The pyrrole aldehyde, halogen Mol ratio for thing, amidine, alkali is：1:1.1:1.5:4.
  9. A kind of 9. method for synthesizing nitrogen-containing compound according to claim 1, it is characterised in that：The nitrogen heterocyclic ring chemical combination Thing includes following synthesis step：S1：Pyrrole aldehyde, halides, alkali and organic solvent, one section of heating response are added in the reactor Time；S2：Amidine and alkali are added into above-mentioned S1 reaction systems, continues heating response and stops heating afterwards for a period of time；S3, to above-mentioned Water is added in S2 reaction systems, ethyl acetate extraction, saturated nacl aqueous solution washing, washing, merges organic phase, anhydrous sodium sulfate Dry, revolving removes solvent, residue silica gel column chromatogram separating purification, and petrol ether/ethyl acetate obtains solid as eluant, eluent.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109232402A (en) * 2018-10-09 2019-01-18 五邑大学 A kind of preparation method for the nitrogenous hexa-member heterocycle class compound that 2- amino replaces

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102933584A (en) * 2010-04-16 2013-02-13 Abbvie公司 Pyrrolopyrazinone inhibitors of kinases

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102933584A (en) * 2010-04-16 2013-02-13 Abbvie公司 Pyrrolopyrazinone inhibitors of kinases

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109232402A (en) * 2018-10-09 2019-01-18 五邑大学 A kind of preparation method for the nitrogenous hexa-member heterocycle class compound that 2- amino replaces

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