- Chiral Phosphoric-Acid-Catalyzed Cascade Prins Cyclization
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Asymmetric Prins cyclization of in situ generated quinone methides and o-aminobenzaldehyde has been developed with chiral phosphoric acid as an efficient catalyst. This unconventional method provides a facile access to diverse functionalized trans-fused pyrano-/furo-tetrahydroquinoline derivatives in excellent yield and with excellent diastereo- and enantioselectivities (up to 99% yield and 99% ee). Mechanistic studies suggested that the three adjacent tertiary stereocenters were constructed through the sequential formation of C-O, C-C, and C-N bonds.
- Sun, Huai-Ri,Zhao, Qingyang,Yang, Hui,Yang, Sen,Gou, Bo-Bo,Chen, Jie,Zhou, Ling
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supporting information
p. 7143 - 7148
(2019/09/07)
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- Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands
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We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.
- Ida, Yoshihiro,Matsubara, Ayaka,Nemoto, Toru,Saito, Manabu,Hirayama, Shigeto,Fujii, Hideaki,Nagase, Hiroshi
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p. 5810 - 5831
(2012/11/06)
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- OXIDATIVE DEGRADATION OF 8-NITROQUINOLINE WITH HYDROGEN PEROXIDE IN ACETIC ACID --- A POSSIBLE MECHANISM THROUGH 3,4-EPOXIDE OF QUINOLINE RING
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The treatment of 8-nitroquinoline with hydrogen peroxide and acetic acid at 60 grad C afforded 7-nitroindole, 7-nitro-2-oxindole, 2-amino-3-nitrobenzoic acid, 2-amino-3-nitrobenzaldehyde, 3,4-dihydro-3,4-trans-dihydroxy-8-nitrocarbostyril, 3,4-trans-dihyd
- Kaiya, Toyo,Kawazoe, Yutaka
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p. 511 - 518
(2007/10/02)
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