- Reactions of 3-Acetyltropolone and Its Methyl Ethers with 1,2-Ethanediamines
-
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.
- Sudoh, Yasunori,Onitsuka, Katsunobu,Imafuku, Kimiaki,Matsumura, Hisashi
-
-
Read Online
- MUSCARINIC ACETYLCHOLINE M1 RECEPTOR ANTAGONISTS
-
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.
- -
-
Paragraph 0364-0366
(2021/04/17)
-
- Direct exchange of a ketone methyl or aryl group to another aryl group through ciC bond activation assisted by rhodium chelation
-
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
- Wang, Jingjing,Chen, Weiqiang,Zuo, Sujing,Liu, Lu,Zhang, Xinrui,Wang, Jianhui
-
supporting information
p. 12334 - 12338
(2013/02/23)
-
- The Thermolysis of Polyazapentadienes. Part 2. Formation of Quinoxalines from 5-Aryl-1-phenyl-1,2,5-triazapentadienes
-
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.
- McNab, Hamish
-
p. 1941 - 1946
(2007/10/02)
-