89334-34-9Relevant academic research and scientific papers
Reactions of 3-Acetyltropolone and Its Methyl Ethers with 1,2-Ethanediamines
Sudoh, Yasunori,Onitsuka, Katsunobu,Imafuku, Kimiaki,Matsumura, Hisashi
, p. 3358 - 3363 (1983)
3-Acetyltropolone reacted with 1,2-ethanediamine to give N,N-bis(3-acetyl-2-oxo-3,5,7-cycloheptatrienyl)-1,2-ethanediamine (3) and 5-acetyl-3,4-dihydro-2H-cycloheptapyrazine (4), along with a small amount of by-products, which were 8-acetyl-1,2,3,4-tetrahydro-5-quinoxalinecarbaldehyde (5), 5-acetyl-1,2,3,4-tetrahydroquinoxaline (6), and 2-methyl-5,6-dihydro-4H-pyrroloquinoxaline (7).The minor products (5-7) resulted from the contraction of the seven-membered ring of the compound 4. 2-Acetyl-7-methoxytropone (2a) also reacted with 1,2-ethanediamine to give the same products (3-7) in higher yields.On the other hand, the same reaction of 3-acetyl-2-methoxytropone (2b) readily gave 4-7.The reaction of 2a with N-methyl-1,2-ethanediamine gave N-(3-acetyl-2-oxo-3,5,7-cycloheptatrienyl)-N'-methyl-1,2-ethanediamine (14), 5-acetyl-1-methyl-2,3-dihydro-1H-cycloheptapyrazine (15), 8-acetyl-4-methyl-1,2,3,4-tetrahydro-5-quinoxalinecarbaldehyde (16), 5-acetyl-1-methyl-1,2,3,4-tetrahydroquinoxaline (17), and 2,6-dimethyl-5,6-dihydro-4H-pyroloquinoxaline (18).The same reaction of 2b also gave the products (15-18).The several reactions of these products are also described.
MUSCARINIC ACETYLCHOLINE M1 RECEPTOR ANTAGONISTS
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Paragraph 0364-0366, (2021/04/17)
Provided herein, inter alia, are compounds which are useful as antagonists of the muscarinic acetylcholine receptor M1 (mAChR M1); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with muscarinic acetylcholine receptor dysfunction using the compounds and compositions.
Direct exchange of a ketone methyl or aryl group to another aryl group through ciC bond activation assisted by rhodium chelation
Wang, Jingjing,Chen, Weiqiang,Zuo, Sujing,Liu, Lu,Zhang, Xinrui,Wang, Jianhui
supporting information, p. 12334 - 12338 (2013/02/23)
Swapped: Commercially available quinolinone derivatives (1 or 2, see scheme) were reacted with arylboronic acids in the presence of a RhI complex to give aryl(quinolin-8-yl)methanone products 3 in medium to good yields. A mechanism that involves the in situ oxidation of RhI to RhIII by O2 in the presence of CuI was proposed. Copyright
The Thermolysis of Polyazapentadienes. Part 2. Formation of Quinoxalines from 5-Aryl-1-phenyl-1,2,5-triazapentadienes
McNab, Hamish
, p. 1941 - 1946 (2007/10/02)
Thermolysis in the gas phase of 5-(p-substituted phenyl)-1-phenyl-1,2,5-triazapentadienes at 600 deg C and 10-2 Torr gives 6-substituted quinoxalines.The yield is ca. 30 percent, and is independent of the electronic nature of the substituent.The corresponding 5-(o-substituted) derivatives give 5-substituted quinoxalines, though the yield is lower, and quinoxaline itself is a major contaminant, due to ipso attack and ejection of the substituent. 5-(m-Substituted) derivatives give mixtures of 5- and 6-substituted quinoxalines on pyrolysis.The 5-isomer is dominant for compounds with m-alkyl substituents, while the 6-isomer is the major product for those with electron-withdrawing or electron-donating m-substituents.
