Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 22, Problem 22.62P
A newer generation of antipsychotics, among them clozapine, are now used to treat the symptoms of schizophrenia. These drugs are more effective than earlier drugs in improving patient response in the areas of social withdrawal, apathy, memory, comprehension, and judgment. They also produce fewer side effects such as seizures and tardive dyskinesia (involuntary body movements). In the following synthesis of clozapine, Step 1 is an Ullmann coupling, a type of nucleophilic
- (a) Show how you might bring about formation of the amide in Step 2.
- (b) Propose a reagent for Step 3.
- (c) Propose a mechanism for Step 4.
- (d) Is clozapine chiral? If so, how many of the possible stereoisomers are formed in this synthesis?
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Paroxetine (Paxil) is an antidepressant that is a member of a family of drugs known
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F
НО
SOCI,
A
B
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Prostaglandins are a class of eicosanoids, fatty acid derivatives involved in a variety of important phenomena, including fever, inflammation, and pain. The first step in
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Ibuprofen is one of several inhibitors of cyclooxogenase used therapeutically.
Arachidonic acid
20₂
0.5
1.0
1.5
2.5
3.5
cyclooxrygenase
PGG₂
JOH
محمد
The following kinetic data were obtained for the enzyme cyclooxygenase in the absence of any inhibitor (1), and in the presence of ibuprofen (2) at a concentration of 48
[arachidonic acid] (uM)
(1) v(uM/min) (2) v(uM/min)
23.5
32.2
36.9
41.8
44.0
16.67
25.25
30.49
37.04
38.91
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Estrogens are female sex hormones, the most potent of which is B-estradiol.
OH
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In recent years, chemists have focused on designing and synthesizing molecules that
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antagonists, compounds that interact with estrogen receptors and block the effects of
both endogenous and exogenous estrogens. A feature common to one type of nonste-
roidal estrogen antagonist is the presence of a 1,2-diphenylethylene with one of the
benzene rings bearing a dialkylaminoethoxyl substituent. The first nonsteroidal estrogen
antagonist of this type to achieve clinical importance was tamoxifen, now an important
drug in the treatment of breast cancer. Tamoxifen has the Z configuration shown here.
NMeg
A
B
NMeg ?
ОН
Tamoxifen
Propose reagents for the conversion of A to tamoxifen. Note: The final step in this
synthesis gives a mixture of E and Z isomers.
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 22.1PCh. 22.1 - Write a structural formula for the product from...Ch. 22.1 - Prob. 22.3PCh. 22.2 - Prob. 22.4PCh. 22.2 - Predict the major produce(s) of each electrophilic...Ch. 22.3 - In SN2 reactions of haloalkanes, the order of...Ch. 22 - Prob. 22.8PCh. 22 - Prob. 22.9PCh. 22 - Addition of m-xylene to the strongly acidic...Ch. 22 - Addition of tert-butylbenzene to the strongly...
Ch. 22 - What product do you predict from the reaction of...Ch. 22 - Other groups besides H+ can act as leaving groups...Ch. 22 - Prob. 22.14PCh. 22 - Prob. 22.15PCh. 22 - Prob. 22.16PCh. 22 - Prob. 22.17PCh. 22 - Suggest a reason why the nitroso group, N=O, is...Ch. 22 - Prob. 22.19PCh. 22 - Prob. 22.20PCh. 22 - The following molecules each contain two aromatic...Ch. 22 - Prob. 22.22PCh. 22 - Prob. 22.23PCh. 22 - The insecticide DDT is prepared by the following...Ch. 22 - Prob. 22.25PCh. 22 - Prob. 22.26PCh. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Prob. 22.32PCh. 22 - Show how to prepare each compound from...Ch. 22 - Prob. 22.34PCh. 22 - Show reagents and conditions to bring about the...Ch. 22 - Prob. 22.36PCh. 22 - Propose a synthesis for each compound from...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - Prob. 22.40PCh. 22 - Prob. 22.41PCh. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - Cancer of the prostate is the second leading cause...Ch. 22 - Prob. 22.45PCh. 22 - Prob. 22.46PCh. 22 - Prob. 22.47PCh. 22 - When certain aromatic compounds are treated with...Ch. 22 - Prob. 22.49PCh. 22 - Following is the structure of miconazole, the...Ch. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Show how the antidepressant venlafaxine (Effexor)...Ch. 22 - Prob. 22.57PCh. 22 - Given this retrosynthetic analysis, propose a...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - A newer generation of antipsychotics, among them...Ch. 22 - Prob. 22.63P
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