An approach to alicyclic ring-fused xanthines

Article abstract of DOI:10.1016/j.tet.2012.08.014

A convenient three-step approach to the synthesis of five to eight-membered alicyclic ring-fused xanthines was developed. The method included reaction of lactim or thiolactim ethers with 6-aminouracils, followed by bromination and copper-catalyzed arylation. The procedure allowed preparation of the title compounds in 21-36% overall yields.

Full text of DOI:10.1016/j.tet.2012.08.014

SUPPORTING INFORMATION
An approach to alicyclic ring-fused xantines
Kostiantyn Liubchak*, Andrey Tolmachev, Oleksandr O. Grygorenko, and
Kostiantyn Nazarenko
Corresponding author. Tel.: +380 50 707 12 10; e-mail: kliubchak@gmail.com
Content:
1. Copies of 1H and 13C NMR spectra for compounds 7aa-7dc – page S2 – S13
2. Copies of 1H and 13C NMR spectra for compounds 4aa-4dc – page S14 – S25
3. Copies of 1H and 13C NMR spectra for compounds 3aa-3dc – page S25 – S37
S1

S2

S3

S4

S5

S6

S7

S8

S9

S10

S11

S12

S13

S14

S15

S16

S17

S18

Phlk-517.fid
N
O
O
N
N
N
Br
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
File name: Phlk-517.fid
Operator:
SF: 399.9683 MHz
SW: 6803 Hz
NSC: 0
PW: 7.50 usec, RG: 22
AQ: 1.33 sec, RD: 0.00 sec
SI: 32768
Date: 01-Mar-2011
Solvent: cdcl3
TE: 293 K
PHlk-517-C13
O
N
N
N
O
N
Br
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
0
File name: PHlk-517-C13
Operator: root
SF: 125.7422 MHz
NSC: 108
PW: 0.00 usec, RG: 51200
SI: 6553
S19

S20

S21

S22

S23

CH
3
CH
3
N
N
O
NH
Br
NH
O
PHlk532
1.31
11.0
1.34
1.51 2.75
3.5
2.06
2.5
1.35 3.92
6.00
1.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.0
2.0
1.5
0.5
0
Chemical Shift (ppm)
CH
3
CH
3
N
N
O
NH
Br
NH
O
PHlk-532-APTC13_001000fid
160
152
144
136
128
120
112
104
96
88
80
72
64
56
48
40
32
24
16
8
0
Chemical Shift (ppm)
S24

S25

S26

S27

S28

S29

S30