Tổng hợp một số xeton anpha,beta-không no từ 3-Axetyl-2-metylbenzo[f]Cromon = Synthesis of some alpha,beta-unsaturated ketones from 3-acetyl-2-methylbenzo[f]chromone

TAP CHI HOA HOC T. 50(2)239-244 THANG 4 NAM 2012

T6N G Hgp MOT S6 XETON ff,^KH6NG NO TLK

3-AXETYL-2-IVIETYLBENZO[/]CROMON

Duong Nggc Todn'*, Le Van Thuan\ Nguyen Minh Thao^

'Khoa Hda hgc, Truong Dgt hgc Suphgm Thdi Nguyen

^Truong THPT Ltiung Tdi. Bdc Ninh

^Khoa Hod hgc. Trirang Dgi hgc Khoa hgc Tu nhien. DHQG Hd Ngi

Den Tda soan 22-02-2012

Abstract

By cyclization reaction of l-acetyl-2-hidroxynaphthalene with anhydride acetic to get 3-acetyl-2-

methylbenzo|/|chromone. The product was then transft)rmed by condensation wilh aromatic aldehydes to form a series

of new a,^-unsaturated ketones (7 compounds) and (2-arylvinylbenzo[/]chromone-3-yl)aryl vinyl ketones

(4 compounds). Stmcture of the obtained products were confimed by IR, 'H NMR, '^C NMR, HSQC, HMBC and MS

spectroscopic data. The biological activities of these compounds have been investigated.

I. MO DAU khdng no tir 3-axetyl-2-metylbenzocromon.

Cromon vd dan xudt ciia nd dugc biat den Id hgp

chat di vong chira oxi quan trgng trong tg nhian.

Mot so hgp chat trong tu nhian vd tdng hgp chira

khung cromon cd boat tinh sinh hgc quy, chang han

nhir lie cha su phdt trien cua khdi u [I], chdng oxi

hoa [2] vd cd tdc dung khdng khudn, chong nam [3].

Nhieu cdng trinh nghien ciru ve boat tinh sinh

hoc cua cac xeton a;^khdng no deu da khang djnh

chung hau het cd hogt tinh khdng khudn, khdng nam,

ngoai ra con cd nhu-ng hgp chat the hien cd khd nang

diet CO va chdng ung thu gan, phdi [4-6]. Bai viet

nay trinh bdy ket qud tdng hgp cdc xeton 0,(3-

2. THUC NGHIEM

Phd IR ciia cdc hgp chit tong hop dugc do tren

mdy Impact 410-NieoIet, do d dgng ep vian vdi KBr

tgi Vipn Hda hgc, Vien Khoa hgc vd Cong nghe Viet

Nam. Phd NMR do tran mdy Bruker XL-500 trong

DMSO-de tgi Vipn Hda hgc, Vipn Khoa hgc vd Cdng

nghe Viet Nam. Phd MS do tren may AutoSpec

Premier, USA, Khoa Hda hgc, Trudng Dai hgc

Khoa hgc Ty nhien, DHQG Ha Ngi.

Da tdng hgp dan xuat 3-axetyl-2-

metyIbenzo[/]cromon chung tdi da thyc hien mgt

chu6i phdn u'ng theo so dd phdn ii'ng nhu sau:

2-L long hgp ^-naphtyl axetat va l-axetyl-2-

liiSroxinaphtalen: dugc tdng hgp theo tai lipu [7].

2-2. Tong hop 3-axetyl-2-metyIbenzo[/]cromon (I)

Cho vao binh can day trdn cd ldp sinh hdn hoi

'f" h6n hgp ciia 7,7 gam l-axetyl-2-

i'idroxinaphtalen, 15 gam natri axetat vd 25 ml

anhidrit axetic. Dun hoi luu hdn hgp phan irng trong

sudt 8-10 gid d 130-140°C. Da ngudi hdn hgp phan

irng dan nhiet dg phdng, dd hdn hgp phdn img vao

coc nudc dd, khuay manh, kat tua tao ra dugc lgc hut

va kat tinh lai bdi etanol. San pham thu dugc la chat

ran mau vang nau, cd diem ndng chdy 164-I65*'C,

hipu suit phdn ung dgt khodng 35%.

2.3. Phuong phap chung tong hgp cac xeton

a,/?-kh6ng no (IIi.?) [3]

Cho vao binh cdu ddy trdn 0,005 moi hgp chat