Isoquinolinium salt syntheses from cyclopalladated benzaldimines and alkynes

1988 ◽  
Vol 53 (14) ◽  
pp. 3238-3241 ◽  
Author(s):  
Guangzhong Wu ◽  
Steven J. Geib ◽  
Arnold L. Rheingold ◽  
Richard F. Heck
Keyword(s):  
Isoquinolinium Salt

Design, Synthesis, and Applications of a Novel Fluoride Probe Based on Isoquinolinium Salt

2020 ◽  
Vol 90 (8) ◽  
pp. 1518-1522 ◽  
Author(s):  
Yeting Zhu ◽  
Yajun Yu ◽  
Yun-Hui Zhao ◽  
Zilong Tang ◽  
Li Tian
Keyword(s):  
Design Synthesis ◽  
Isoquinolinium Salt

ChemInform Abstract: Isoquinolinium Salt Syntheses from Cyclopalladated Benzaldimines and Alkynes.

ChemInform ◽  
1988 ◽  
Vol 19 (51) ◽  
Author(s):  
G. WU ◽  
S. J. GEIB ◽  
A. L. RHEINGOLD ◽  
R. F. HECK
Keyword(s):  
Isoquinolinium Salt

Photo-induced crystallization with emission enhancement (PICEE)

2020 ◽  
Vol 7 (11) ◽  
pp. 3005-3010
Author(s):  
Kongqi Chen ◽  
Rongyuan Zhang ◽  
Ganggang Li ◽  
Baoxi Li ◽  
Yao Ma ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Emission Enhancement ◽  
Isoquinolinium Salt ◽  
Mitochondria Targeting ◽  
Induced Crystallization

A new photoactivation mechanism, photo-induced crystallization with emission enhancement, is developed based on an isoquinolinium salt with applications in mitochondria-targeting and photodynamic therapy.

Photosolvolysis of Bridgehead Quaternary Ammonium Salts. III. Synthesis of Some 3-Benzazecine, 1H-2,6-Benzoxazecine and 2H-3,6-Benzoxazecine Derivatives and a 2H-1,4-Oxazocine Derivative

1985 ◽  
Vol 38 (11) ◽  
pp. 1591 ◽  
Author(s):  
JB Bremner ◽  
KN Winzenberg
Keyword(s):  
Chloroform Solution ◽  
Chair Conformation ◽  
Ring System ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
High Yield ◽  
Methyl Derivative ◽  
Isoquinolinium Salt ◽  
Cis And Trans ◽  
Twist Boat

Photosolvolysis of a mixture of cis - and trans-9,10-dimethoxy-5-methyl- 1,3,4,6,7,11b-hexahydro-2H-benzo[a] quinolizinium iodide (2) in methanol gave, after workup, a very low yield of 8,10,11-trimethoxy-3-methyl- 1,2,3,4,5,6,7,8-octahydro-3-benzazecine (3a). Similarly 1,10,11 trimethoxy-6-methyl-3,4,5,6,7,8-hexahydro-1H-2,6-benzoxazecine (8a) and 1,10,11-trimethoxy-6-methyl-1,4,5,6,7,8-hexahydro-2H-3,6-benzoxazecine (16a) were obtained in fair and low yields respectively from the N- methyl tetrahydro-2H,6H-[1,3] oxazino [2,3-a] isoquinolinium (7a) and hexahydro [1,4] oxazino [3,4-a] isoquinolinium (15) iodide precursors; a 1- methyl derivative (8b) of (8a) was also prepared. The ring-opened products 3-[N-2-{(4,5-dimethoxy-2-dimethoxymethyl)-phenyl}ethyl-N-methyl]aminopropan-1-ol (9a) and 3-[N-2-{(4,5-dimethoxy-2-1′,1′- dimethoxyethyl )-phenyl}ethyl-N-methyl]aminopropan-1-ol (9b) were also obtained from the [1,3] oxazino [2,3-a]- isoquinolinium salt derivatives. Photolysis of (2) and 9,10-dimethoxy-5-methyl-1,3,4,6,7,11b-hexa-hydro[1,4] oxazino [3,4-a] isoquinolinium iodide (15) in acidified aqueous solution afforded, after workup, the benzazecin-8-ol (3b) and hexahydro-2H-3,6-benzoxazecin-1-ol (16b) products respectively, but again in very low yield. Some mechanistic rationalizations of these results are given.Photosolvolysis of 7a-(3,4-dimethoxy)phenyl-4-methyl-2,3,5,6,7,7a- hexahydropyrrolo [2,1-b] oxa-zolium iodide (22) in methanol afforded a high yield of 8-methoxy-4-methyl-8-(3,4-dimethoxy)-phenyl-3,4,5,6,7,8- hexahydro-2H-1,4-oxazocine (24) in a new ring-destruction approach to this ring system. From 13C n.m.r . data, the twist-boat-chair conformation was tentatively assigned to (24) in (D)chloroform solution.

scholarly journals Studies on 1,2,3,4-tetrahydroisoquinolines. II. A one-pot synthesis of 1-arylmethyl-1,2,3,4-tetrahydroisoquinolines from an isoquinolinium salt.

1981 ◽  
Vol 29 (7) ◽  
pp. 1848-1853 ◽  
Author(s):  
KOICHIRO YAMADA ◽  
NOBUO ITOH ◽  
KATSUO IKEZAWA ◽  
AKIO KIYOMOTO ◽  
TAKEO IWAKUMA
Keyword(s):  
One Pot ◽  
One Pot Synthesis ◽  
Isoquinolinium Salt

Glycosidase-catalyzed hydrolysis of 2-deoxyglucopyranosyl pyridinium salts: effect of the 2-OH group on binding and catalysis

2000 ◽  
Vol 78 (5) ◽  
pp. 577-582 ◽  
Author(s):  
Kelly SE Tanaka ◽  
Jiang Zhu ◽  
Xicai Huang ◽  
Francesco Lipari ◽  
Andrew J Bennet
Keyword(s):  
Active Site ◽  
Pyridinium Salts ◽  
Transition State Stabilization ◽  
Glycosidase Inhibitor ◽  
Isoquinolinium Salt ◽  
Relative Transition ◽  
Catalyzed Reactions ◽  
Hydrolysis Of ◽  
Spontaneous Reaction ◽  
Reaction In Solution

Three 2-deoxy-α-D-glucopyranosyl pyridinium tetrafluoroborates were tested for their binding affinity to a range of α-glucosidases and α-mannosidases. The α-isoquinolinium salt (11) binds approximately 275-fold more tightly to yeast α-glucosidase than does the isomeric quinolinium salt (12). In addition, compound 11 binds to the yeast enzyme approximately two-fold tighter than the corresponding glucopyranosyl isoquinolinium salt (9). The (kcat/khyd) values for the yeast α-glucosidase-catalyzed reactions of 11 and 9 are 1.6 × 105 and 2.0 × 109, respectively, when compared to the spontaneous uncatalyzed reactions. Thus, the interaction of the 2-OH group in compound 9 with the yeast enzyme's active site generates a relative transition state stabilization of about 23.5 kJ mol-1. For both compounds 11 and 12, the observed rate accelerations for the yeast α-glucosidase-catalyzed hydrolysis, relative to the spontaneous reaction in solution, (kcat/khyd) are identical within experimental error.Key words: glycosidase, inhibitor, 2-deoxyglucose, pyridinium, catalysis.

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