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Journal of Babylon University/Pure and Applied Sciences/ No.(1)/ Vol.(21): 2013

absorption bands at3190cm-1 ,3160cm-1,3050cm-1 and attributed to the υ (C-H) aromatic of benzene ring. The absorption bands at 3385 cm-1 and 3320cm-1 attributed to the υ(O-H). FT-IR spectrum of tetrazole derivative [9] showed disappearance of the strong absorption band at 1618 cm-1due to the υ(C=N) exocyclic and appearance of medium absorption band at 1700cm-1 due to the υ(C=N) inside tetrazole ring ( Firrozi et.al.,1995 and Salih,2005).Beside this FT-IR spectrum of tetrazole derivative [9] was devoid of a strong band at 2160-2120 cm -1 attributed to the stretching vibration of azide group (-N3) .FT-IR spectrum of compound [9] showed appearance of the following absorption bands: The strong absorption band at 1604 cm-1 attributed to the υ(C=N) inside thiadiazole ring. The medium absorption band at 1487 cm-1 attributed

to the υ ( C C) aromatic of benzene ring. The medium absorption band 1370 cm-1 attributed to the δ (C-H) aliphatic of butyl group . The medium absorption band at 1315cm-1 attributed to the δ (O-H) in plane. The strong absorption bands 1176 cm-1 attributed to the υ(C-O) of phenol. The weak absorption band at 1080 cm-1 due to the υ(N-N) inside tetrazole and thiadiazole rings. The strong absorption band at 829 cm-1 due to due to the δ(C-H) aromatic out of plane. The medium absorption band at 740cm-1 attributed to the δ (O-H) out of plane. The two weak absorption bands at 630 cm-1 and 595 cm-1 attributed to the υ(C-S). The medium absorption band at 2914 cm-1 attributed to the υ (C-H) aliphatic of butyl group.The weak absorption band at 3150cm- 1 attributed to the υ (C-H) aromatic of benzene ring. The two sharp strong absorption bands at 3417cm-1 and 3273 cm-1 attributed to the υ(O-H). FT-IR spectrum of oxazepine derivative [10] showed appearance of two interacted absorption bands at 1697 cm-1and 1680 cm-1 attributed to the υ (C=O) of lactone and lactam groups inside oxazepine ring, respectively .The strong absorption band at 1606cm-1 due to the υ(C=N) inside thiadiazole ring. The strong absorption band at 1500 cm-1 due to the υ

( C C) aromatic of benzene ring.The medium absorption band at 1392cm-1 attributed to the δ (O-H) in plane. The absorption bands at 1290cm-1 and 1278 cm-1 attributed to the δ (C-H) aromatic in plane. The absorption bands at 1195 cm-1 and 1090 cm-1 attributed to the υ(C-O) of phenol and lactone, respectively. The strong absorption band at 1020 cm-1 due to the υ(N-N) inside thiadiazole ring. The three absorption bands at 891cm-1 , 835 cm-1 and 752cm-1 attributed to the δ (C-H) aromatic out of plane. The absorption band at 677cm-1 due to the δ (O-H) out of plane. The weak band at 597 cm-1 attributed to the υ(C-S).The two absorption bands at 3412cm- 1and 3390cm-1 attributed to the

υ(O-H) . The weak absorption bands at 3180cm-1 , 3091cm-1 and 3000cm-1 due to the

υ(C-H) aromatic of benzene ring out of plane. The weak absorption bands at 2970cm-

1 , 2940cm-1 , 2872cm-1 and 2800cm-1 attributed to the υ (C-H) aliphatic of (-CH2-) groups. FT-IR spectrum of oxazepine derivative [11] showed appearance of two interacted absorption bands at 1720 cm-1and 1690 cm-1 attributed to the υ (C=O) of lactone and lactam inside oxazepine ring, respectively .The absorption band at 1612cm- 1 attributed to the υ(C=N) inside thiadiazole ring. The medium absorption band at

1490 cm-1 due to the υ( C C) aromatic of benzene ring. The weak absorption band at 1450cm-1 due to the δ (C-H) aliphatic of (-CH2-) group. The weak absorption bands at 1400cm-1 due to the δ (O-H) in planeThe strong absorption bands at 1182cm-1 and 1110 cm-1 attributed to the υ(C-O) of phenol and lactone, respectively. The strong absorption band at 1010 cm-1 due to the υ(N-N) inside thiadiazole ring. The two absorption bands at 887cm-1 and 825 cm-1 attributed to the δ (C-H) aromatic out of plane. The absorption band at 700 cm-1 due to the δ (O-H) out of plane. The weak band at 611 cm-1 attributed to the υ(C-S).The absorption band at 3215cm-1 attributed

191

to the υ (O-H).The weak absorption bands at 3120cm-1 and 3020cm-1 attributed to the υ (C-H) aromatic. The weak absorption bands at 2940cm-1 , 2880cm-1,2850cm-1 and 2800cm-1 attributed to the υ (C-H) aliphatic of (-CH2-) group. FT-IR spectrum of terazole derivative [12] showed disappearance of the strong absorption band at 1653 cm-1 due to the υ (C=N) exocyclic and appearance of strong absorption band at1716 cm-1 due to the υ (C=N) inside tetrazole ring.(Firrozi et.al., 1995 and Salih, 2005).Beside this FT-IR spectrum of tetrazole derivative [12] was devoid of a strong band at 2160-2120 cm -1 due to the υ(-N3). The absorption band at 1625cm-1 attributed to the υ(C=N) inside thiadiazole ring. The medium absorption bands at 1590 cm-1 ,

1530 cm-1 and 1490 cm-1 attributed to the υ ( C C) aromatic of benzene ring . The absorption bands at 1450cm-1 and 1375cm-1 attributed to the υ (C-H) aliphatic. The absorption band at 1335cm-1 due to the δ (O-H) in plane. The strong absorption band at 1226 cm-1 attributed to the δ(C-H) aromatic of benzene ring in plane. The medium absorption band at 1170 cm-1 due to the υ(C-O) of phenol. The strong absorption band at 1030 cm-1 due to the υ(N-N) inside tetrazole and thiadiazole rings. The strong absorption band at 900cm-1 attributed to the δ (C-H) aromatic of benzene ring out of plane. The weak absorption band at 710cm-1 attributed to the δ (O-H) out of plane. The medium absorption band at 615 cm-1 attributed to the υ(C-S). The two sharp absorption bands at 3269cm-1 and 3200cm-1 attributed to the υ (O-H) groups . The three weak absorption bands at 3150cm-1 ,3070cm-1 and 3020cm-1 attributed to the υ (C-H) aromatic of benzene ring. The weak absorption bands at 2980cm-1 , 2940cm-1 , 2870cm-1 and 2800cm-1 attributed to the υ (C-H) aliphatic.

192

Journal of Babylon University/Pure and Applied Sciences/ No.(1)/ Vol.(21): 2013

H2N NH2

/HCl

0

 

C

2

(0-5)

NaNO

 

 

Cl N N

H -O

/

HO

OHC

N N Cl

(0-5)0C

N N N N

O O

HO

[ 1 ]

OH

N N

H2N S S

[ 3 ]

N N

S S

abs.EtOH,reflux

 

 

abs.EtOH,reflux

N N

N

N N

N N

S S

 

 

 

HO

[ 6 ]

 

 

 

 

 

N N

N N

N

N N

 

N S

 

 

 

HO

[ 5 ]

 

 

OH

N N

H2NS S

[ 4 ]

N N

N S S

OH

S

193

N N

N N

N N

N

N N

S S

 

N S S

 

HO

[ 5 ]

 

 

OH

NaN

 

dioxan,reflux

 

O

O O

3

 

 

 

 

 

N

 

N

 

N

 

 

 

 

N N

 

N N N

 

 

N

 

 

N N N N

N

S S

 

 

 

N

N

 

HO

[ 9]

S

 

 

 

OH

S

 

 

 

 

 

x

 

 

 

 

 

x

 

u

 

 

 

 

 

u

 

l

 

 

 

 

 

l

 

f

 

 

 

 

 

f

 

e

 

 

 

 

 

e

 

r

 

 

 

 

 

r

 

,

 

 

 

 

 

,

 

e

 

 

O

 

O

e

 

n

 

 

O

n

 

e

 

 

 

e

 

z

 

 

 

 

z

 

n

 

 

 

 

 

n

 

e

 

 

 

 

 

e

 

b

 

 

 

 

 

b

 

y

 

 

 

 

 

y

 

r

 

 

 

 

 

r

 

d

 

 

 

 

 

d

 

S

N

 

 

 

 

N

S

 

 

 

N

 

 

N

N N

 

N N

S O

O S

 

 

 

N

 

 

 

 

N

 

 

O

OH

[ 7 ]

HO

 

O

 

 

O

 

 

O

 

 

 

 

 

 

 

S N

 

 

N

S

 

N

N N

N N

N

S

O

S

 

 

 

 

N

 

 

N

O

 

 

 

 

 

O

 

 

 

[ 8 ]

O

 

 

 

HO

OH

 

 

 

O

 

O

 

194

Journal of Babylon University/Pure and Applied Sciences/ No.(1)/ Vol.(21): 2013

N N

N N N NN N

N N S S S S

[ 6]

NaN

dioxan,reflux

3

 

NN

N N

N N SS

HO

HO

 

 

lux

 

 

,ref

O

O O

benzene

 

 

 

dry

NN N N

N NN N NNSS

[ 12 ]

OH

OH

 

 

 

 

lux

 

 

O

O O

ene,ref

 

 

 

 

drybenz

N

 

 

 

N S

S

N

 

 

N SO

OS

N N

N N

N

 

 

 

N

O

[ 10 ]

HO O

OH

O

 

 

 

O

S

N

 

 

N S

S

N

N N

N N

N S

 

O N

 

 

N O

 

O

 

 

 

 

 

O

 

HO

 

[ 11]

OH

 

O

 

O

Scheme(3):Reactionspathway

195

S

 

 

N

 

 

 

 

 

 

N

H

 

 

N

 

 

 

 

N

 

 

1)Na CO ,CS

/abs.EtOH,reflux

Tautomerism

 

2 3 2

 

 

 

 

 

 

 

H2N-C

-NHNH2 + CS2

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

2(Conc.HCl

H2N

S

SH

 

 

H2N

S

S

[ 2]

H

 

 

 

 

 

 

 

H

 

O

 

x

x

 

O

K

 

u

u

 

l

K

l

,

 

f

f

e

 

e

,

 

e

 

r

e

r

d

,

,

i

 

n

d

n

r

 

a

i

a

o

 

m

l

 

x

x

h

 

o

o

o

c

 

i

r

i

l

 

d

b

d

 

y

l

y

y

 

z

 

r

y

r

n

 

d

u

d

e

 

 

t

 

 

 

b

 

b

 

 

-

 

 

 

 

 

n

 

 

 

 

 

 

 

 

 

 

 

 

 

N N

N

N

 

 

H2N S S

H2N S

S

[ 4 ]

 

[ 3]

Scheme(4):Reactions pathway of preparation the primary amines

[ 3] and [ 4].

196

Journal of Babylon University/Pure and Applied Sciences/ No.(1)/ Vol.(21): 2013

197

FT-IR spectrum of compound [1]

FT-IR spectrum of compound [2]

198

Journal of Babylon University/Pure and Applied Sciences/ No.(1)/ Vol.(21): 2013

FT-IR spectrum of compound [3]

FT-IR spectrum of compound [٤]

199

FT-IR spectrum of compound [5]

FT-IR spectrum of compound [6]

200

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