ASSIGNMENT TITLE

Research paper structures

(ASSIGNMENT #1...SEMESTER FALL-2019)

Submission Date (September 18, 2019)

BY

Umar Zulfiqar

16361507-025

Research Methodologies

BS VII CHEMISTRY

Dr. Ghulam Mustafa

Department of Chemistry

UNIVERSITY OF GUJRAT

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Novel 1,4-benzothiazin derivatives: synthesis, crystal structure,
and anti-bacterial properties

Scheme 1

SH S S
a b

NH2 N O N O
H H
1 2 3

Preparation of 1,4-benzothiazine 2 and 2-(phenylmethylidene)-3,4-dihydro-2H-1,4-

benzothiazin-3-one 3. Reagents and conditions: (a) ClCH3CO2CH3, DMF/K2CO3,
TBAB, rt, 24h; (b) benzaldehyde, CH3ONa/DMF, reflux 48hrs.

Scheme 2

S S
R i R
N O N O
H R

Scheme 2 Synthetic route for the preparation of N-alkylated 4-8 compounds, (i) substituted
alkynes (CH3CO2CH3 Cl, CH2 (CH2)2 CH3 Br), DMF, K2CO3, TBAB, rt, 24h.

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Scheme 3

S S
H ii
+ N . HCL
Cl Cl
N O N O
H
3 9
N O
O
Preparation of (2z)-4-[2-(2--oxo-1,3-oxazolin-3-y) ethyl]-2(phenylmethylidene)-3,4-dihydro-2H-
1,4-benzothiazin-3-one 9, (ii) DMF, k2CO3, TBAB, 80 , 6h.

Scheme 4

S S
H
+ N . HCL
Cl Cl
N O O C O N O
H O

3 2K NH

Cl

S S

N O N O

NH O N O
O O O

Plausible mechanism for formation of (2Z)-4-[2-(2--oxo-1,3-oxazolin-3-y) ethyl]-

2(phenylmethylidene)-3,4-dihydro-2H-1,4-benzothiazin-3-one 9.

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Scheme 5

S S
iii R

N O N O
N
N
N
R1

Synthesis of triazolylmethyl benzithiazinone derivatives 10-12. Reagents and conditions: (iii)

substituted azides (R1-N3), CuSO4.5H2O, Sodium ascorbate (5% mol) H2O/EtOH (1:1), rt,
10h.

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References:
 DOI 10.1007/s11164-016-2499-6
 Res Chem intermed (2016) 42:6845-6862

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