Organic Chemistry of Drug Synthesis. Volume 7
( 6 ). The free phenol group on the newly introduced ring is then alkylated withN,4-chloroethylpiperidine to give the basic ethe ...
potassium channels showed early promise as an agent for treating migraine.^2 Lack of recent references suggest that this activit ...
N CH 3 O OCH 3 OCH 3 H 2 O 2 N CH 3 O OCH 3 OCH 3 (^1415) HO [O] NaBH 4 N CH 3 O OCH 3 OCH 3 16 HO Ac 2 O BF 3 N CH 3 O OH OCH ...
B. Quinolines and Their Derivatives Multidrug resistance poses an increasingly important problem for chemotherapy. Several compo ...
( 39 ). Condensation of the product from that reaction with ethyl cyano- acetate in the presence of acid affords the enamine ( 4 ...
incontinence, as well as depression and schizophrenia.^9 The quinoline portion of this compound is prepared by base-catalyzed Pf ...
with ethyl chloroformate ( 57 ). The benzyl carbamate function on nitrogen at the 4 position is next removed by reduction with a ...
Pictet–Spengler method for building a dihydroisoquinoline ring. Thus, treatment of the benzamide ( 61 ) from 2-phenethylamine wi ...
quaternary bromide apparent loses hydrogen bromide under reaction conditions to give the unsaturated quinolone ( 71 ). Treatment ...
reason, been assigned nonproprietary names. By way of a reminder, the quinolones act by interfering with the bacterial enzyme, D ...
of the quinolone ( 85 ). Reaction of 85 with 2-methylpiperazine leads to a second displacement of fluorine, in this case by the ...
The cyclization to a quinolone ( 95 ) in this case is effected with sodium hydride. Treatment of this intermediate with the spi ...
(The reagents used for these last two steps almost guarantee that this is not the route used for larger scale synthesis.) Cataly ...
group is then removed under reductive conditions. This last reaction affords efavirenz( 121 ) as a single enantiomer.^19 Cl NH 2 ...
iodide in the presence of potassium carbonate. The final step involves conversion of the carbonyl group to its sulfur equivalent ...
to afford the dichloro derivative ( 136 ). Treatment with ammonia results in the displacement of the more labile halogen to give ...
O O R CO^2 C^2 H^5 R 140 HNO 3 2. H 2 R = CH 3 OCH 2 CH 2 – O O R CO^2 C^2 H^5 R 141 NH 2 HCO 2 – NH 4 + O O R R 142 N NH O O ...
benzene is next displaced with the alkoxide from the morpholylpropyl alcohol ( 151 ) to afford the ether 152. Catalytic hydrogen ...
Displacement of that halogen by the amine on the aniline ( 170 ) adds the final ring affording 171.^25 N CH 3 O N HO O 163 OCOC( ...
of the quinazoline involves first alkylation of the nitrophenol ( 172 ) with the benzyl bromide ( 173 ) to afford the ether ( 17 ...
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