Tổng hợp một số dẫn xuất 5-Aryl-3-(4-Metylcumarin-3-YL)-1-(4-Nitronphenyl)-3-Pirazolin

TAP CHI HOA HOC T. 51(1)91-95 THANG 2 NAM 2013

T6N G Hgp MOT S6 DAN XUAT 5-ARYL-3-(4-METYLCUIVIARIN-3-YL)-1-

(4-NITROPHENYL)-3-PIRAZOLIN

Du-ffng Nggc Toan'*, Nguyen Minh Thao', Nguyen Thi Minh Thu^, Nguyen Nggc Thanh^

'Khoa Hda hgc, Tnrdng Dgi hgc Suphgm Thdi Nguyen

Khoa Hod hgc, Trudng Dgi hgc Khaa hgc Tu nhien - DHQG Hd Ngi

Khoa Cdng ngh? Hod, Tnrdng Dai hgc Cdng nghi?p Hd Ngi

Den Tda sogn 12-12-2012

Abstract

Five new 5-aryl-3-(4-melhylcoumarin-3-yl)-l-(4-nitrophenyl)-3-pyrazolines have been synthesized by reaction of

3-aryl-l-(4'-methylcoumarin-3'-yl)prop-2-enones with p-nitrophenyihydrazine. The purity and structure of the obtained

products have been confimed by thin layer chromatography, IR, 'H NMR, '^C NMR, HSQC and HMBC spectra.

Keywords; Pyrazolines, methylcoumarin.

1. MO DAU 2. THUC NGHIEM

Dan xuat pirazolin la nhibig hgp chat cd vj tri

quan trgng trong hda dugc. Da sd chiing cd hoat

tinh sinh hgc dang chii y nhu khang khuan, khang

nam, gay me, giam cang ca, chdng tang huyet ap,

chdng suy nhugc, trj benh than kinh... [1-3]. Ben

canh do cac hgp chat kieu 1,3,5-triaryIpirazolin cdn

CO nhiJng iing dung khac nhu iam diot phat quang

va la chat van chuyen cac Id trdng trong vat lieu ban

dan ling dung cho pin mat trdi [4-8].

Tiep theo viec tdng hgp va nghien ciru tinh chat

ciia cac xeton o;/3-khdng no di tir 3-axetyl-4-

metylcumarin [9], bai nay trinh bay ket qua ve

chuyin hda cac xeton o;/3-khdng no d tren thanh

cac hgp chat 5-aryl-3-(4-metylcumarin-3-yl)-l-(4-

nitrophenyl)-3-pirazolin.

Cac xeton a,^-khdng no dugc tdng hgp theo tai

lieu [9]. Cac chat chira di vdng 3-pirazolin dugc

long hgp theo phuang phap nhu sau: Dun hdi luu

30-40 gid hon hgp gdm 10"^ mol xeton o;/3-khdng

no tuang iirng vdi 10'^ mol 4-nitrophenylhidrazin

trong 30ml dung mdi etanol tuyet ddi va xuc tac la 5

- 6 giot axit axetic bang. San pham tach ra dugc Igc

but va kk tinh lai trong dung mdi thich hgp den khi

tren ban mdng silicagel chi cho mgt vet ggn va iron.

Phd hong ngoai do dudi dang vien nen vdi KBr

tren may FTS-6000; Phd cdng hudng tir hat nhan

('H NMR, '^C NMR, HSQC, HMBC) dugc do

trong dung moi DMSO-detren may BRUKER XL￾500 tai Vien Hda hgc, Vien Han lam Khoa hgc va

Cdng nghe Viet Nam.

Sa do phan iing:

COCH3 ^^^,^As^COCH=CHAr

o'Tr ^^0^0 (2)

Trong do Ar la: 4-CIC6H4,4-BrC5H4, 4-CH3C6H4,

4-CH30Ci;H4,2-Thienyl

3. KET QUA VA THAO LUAN

Sau khi ket tinh lai, san pham thu dugc d6u d

dang tinh thi cd mau tir vang den nau xam. Do tinh

khilt ciia cac dan chat tdng hgp dugc xac nhan bdi

nhiet do ndng chay, s k ky ban mdng vdi h? dung

mdi n-hexan-etyl axetat vdi ti le 5:3 (theo the tich).

Mgt sd dO' kien vl diiu che, tinh chat vat Ii, phd

hdng ngoai (IR) ciia cac dan xuat tfing hgp dugc

dugc ghi d bang I.