Synthesis of 2-methyl-4-selenoquinazolone, 2-phenylbenzoselenazole, and its derivatives: Dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Faculty of Pure Science of Columbia UniversityChen, Yü-Gwan
Science
Synthesis of 2-methyl-4-selenoquinazolone, 2-phenylbenzoselenazole, and its derivatives: Dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Faculty of Pure Science of Columbia University
Chen, Yü-Gwan
Organic compounds -- Synthesis; Selenium; Thesis (Ph. D.)
H₂C----NH
| | (V)
H₂C C:NH
\ /
Se
The literature for the other normal carbamides is listed in the
bibliography(27).
Selenoantipyrines, selenosaccharine, selenoindigoes have also been
prepared.
Thiophene and its derivatives are of considerable therapeutic interest.
Thiophene itself is found to be useful in lessening the elimination
of sulphuric acid in urine, and is employed in the dermatological
practice. Sodium thiophene sulphonate, thiophenetetra-bromide,
thiophene diiodide, are all medicinals(23).
A number of selenophenes are recorded in the literature. Their relation
to the selenazoles may be easily seen from the following formulas:
CH--CH CH--N
|| || || ||
CH CH CH CH
\ / \ /
Se Se
Selenophene Selenazole
Dimethyl selenophene was prepared from acetonyl acetone and phosphorous
pentaselenide,
CH₃ CH₃
/ /
HC=C HC=C
| \ | \
| OH + P₂Se₅ = | Se
| OH | /
| / HC=C
HC=C \
\ CH₃
CH₃
The compound thus obtained is stated to have the same odor as
thiophene, but no mention is made in regard to its uses(28).
Selenophene was prepared from sodium succinate and phosphorous
triselenide, or by conducting ethylselenide through hot tubes(29).
Some selenazoles find application also in medicine. At present only
the isoazoles are known to have physiological uses. One of them was
prepared from anthraquinone selenocyanide, by the action of ammonia
under pressure(30).
NH₂H N-Se
O ||
C SeCN C
/\ / \ /\ /\ / \ /\
| | | | = | | | | + HCN + H₂O
\/ \ / \/ \/ \ / \/
C C
O O
Another type of azoles, benzoselendiazole (piaselenol) and five of its
derivatives, have been also described as medicinals(31). The diazole
itself has the following structure,
N N
//\ /|\ //\ / \
| | | Se or | || Se
\\/ \|/ \\/ \ /
N N
Diazoles of the following structure are also known, but no data were
found, regarding their physiological action(32):
N-N N-N
/ \ // \\
CH₃C CCH₃ C₆H₅C CC₆H₅
\ / \ /
Se Se
Dimethyl-seleno-diazole Diphenyl-seleno-diazole
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