- A novel synthesis of aryl mesylates via one-pot demethylation-mesylation of aryl methyl ethers using a mixture of phosphorus pentoxide in methanesulfonic acid
-
A simple, efficient, and new method has been developed for the synthesis of aryl mesylates via one-pot demethylation-mesylation of aryl methyl ethers. Treatment of a variety of aryl methyl ethers with a mixture of phosphorus pentoxide in methanesulfonic a
- Kaboudin, Babak,Abedi, Yaghoub
-
experimental part
p. 2025 - 2028
(2009/12/26)
-
- A simple preparation of aryl methanesulfonates by thermal decomposition of dry arenediazonium O-benzenedisulfonimides in methanesulfonic acid
-
Aryl methansulfonates 3 (18 examples) were easily prepared by thermal decomposition of dry arenediazonium o-benzenedisulfonimides 1 in methanesulfonic acid (2). The reactions were carried out at temperatures between 60 and 120°C for times between 0.5 and 8 h. The aryl methanesulfonates were obtained in reproducible yield of 70-90%, with few exceptions. In all cases the o-benzenedisulfonimide (4) could be recovered in good yields which can then be reused to prepare the salts 1. When thermal decomposition of salts 1 was carried out in trifluoromethanesulfonic acid (5) at 90-120°C for 1-2 h, aryl trifluoromethanesulfonates 6 were obtained in 73-78% yield (3 examples).
- Barbero, Margherita,Degani, Iacopo,Dughera, Stefano,Fochi, Rita,Perracino, Paolo
-
-
- Potential photoaffinity labels for tubulin. Synthesis and evaluation of diazocyclohexadienone and azide analogs of colchicine, combretastatin, and 3,4,5-trimethoxybiphenyl
-
Analogs of tubulin assembly inhibitors such as colchicine, combretastatin, and 3,4,5-trimethoxybiphenyl which incorporate a 6-diazo-2,4-cyclohexadienone (o-quinone diazide) ring have been synthesized and characterized. The compounds synthesized include 6-diazo-4-(2',3',4'-trimethoxyphenyl)cyclohexa-2,4-dien-1-one and its 3-methyl and 3-ethyl analogs (1a-c), 6-diazo-3-(2,3,4-trimethoxyphenyl)-2,4-cyclohexadien-1-one and its 4-methyl and 4-ethyl derivatives (2a-c), 4-[Z-2-(3',4',5'-trimethoxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dienon e (3), 3-[Z-2-(3',4',5'-trimethoxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dien-1 -one (4), the corresponding dihydro derivatives (5, 6) and two isomeric diazocyclohexadienones derived from N-acetylcolchinol (7, 8). Compounds in which the cyclohexadienone oxygen is approximately isostructural with carbonyl or hydroxy functions of the parent compounds exhibit good activity in the tubulin assembly inhibition assay. 2'-Alkyl-4'azido-3,4,5-trimethoxy-1,1'-biphenyls also show good activity as tubulin assembly inhibitors.
- Olszewski,Marshalla,Sabat,Sundberg
-
p. 4285 - 4296
(2007/10/02)
-