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Extending the synthetic utility of p-quinols: hetero Michael-type additions and Friedel-Crafts reactions

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(1)
(2)

Me O

O O

NO 2 H

1 H and 13 C NMR Spectra CHAPTER 2

2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5

8.0 ppm

1.58

2.63 2.64 2.69 2.70

2.99 3.05

4.31 4.32

5.91

6.16 6.20

6.61 6.61 6.64

7.27

7.62 7.65

8.24 8.27 3.13 0.98 1.00 1.00 0.95 1.03 0.98 2.00 2.00

20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190

200 ppm

21.21

38.50

78.5279.30

101.14

123.67

127.21130.12

145.03146.58148.44

194.77

(3)

Me O

O O

H NO

2

1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0

8.5 ppm

1.59

2.702.722.762.783.033.043.093.10

4.464.464.47

5.885.92

6.08

6.476.486.516.52

7.547.57

8.188.21

4.49 2.16 1.00 1.04 1.13 1.07 2.13 2.16

20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190

200 ppm

21.93

37.92

81.40

101.69

123.61126.76127.59

144.33

149.26

194.16

(4)

Me O

O O

CF 3 H

1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5

8.0 ppm

1.62

2.622.632.682.692.972.982.983.033.033.04

4.324.32

5.88

6.156.18

6.606.616.646.65

7.27

7.567.597.647.67

3.15 1.02 0.02 1.02 1.00 0.99 1.01 1.00 4.14

20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190

200 ppm

21.18

38.53

78.2779.17

101.67

118.50122.11125.32125.37125.42125.47125.71126.84127.21129.32130.00130.71131.14131.57132.00142.09142.10146.83151.81

194.96

(5)

Me O

O O

CF 3 H

4 .8 8 7 1 0 .9 9 7 7 1 .0 0 6 0 1 .0 8 3 6 1 .0 0 1 3 1 .1 2 8 8 0 .9 7 7 2 3 .5 9 1 4

In te g ra l 7 .6 3 3 6 7 .6 0 6 1 7 .5 2 2 9 7 .4 9 5 8 6 .5 5 6 4 6 .5 4 8 7 6 .5 2 1 9 6 .5 1 4 2 6 .0 5 8 3 5 .9 5 1 3 5 .9 1 6 8 4 .4 7 8 2 4 .4 7 0 2 4 .4 6 5 4 4 .4 5 8 1 4 .4 5 0 0 3 .1 0 7 5 3 .1 0 4 5 3 .0 9 9 8 3 .0 4 8 1 3 .0 4 5 5 3 .0 4 0 4 2 .7 8 2 7 2 .7 6 9 9 2 .7 2 3 4 2 .7 1 0 9 1 .5 9 8 5

(ppm)

1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0

20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180

190 ppm

26.80

67.68

71.30

125.43125.48126.83127.23

137.99

144.95148.02

152.32

185.44

(6)

Me O

O O

CN H

2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0

7.5 ppm

1.62

2.622.632.682.692.972.972.982.983.023.033.033.04

4.294.304.304.31

5.86

6.156.156.186.19

6.596.606.636.64

7.557.587.587.677.687.70

2.86 1.01 1.03 0.97 0.98 1.01 1.00 0.27 2.10 1.98

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

21.23

38.54

76.6277.0477.4778.4779.29

101.38

113.13

118.48

127.01130.12132.31

143.24146.67

194.85

(7)

2.0000 1.9771 0.9808 0.9503 0.9767 0.9694 0.9827 0.9949 3.3819

Integral 7.6655 7.6376 7.5101 7.4826 6.5249 6.5172 6.4904 6.4827 6.0400 5.9340 5.9311 5.8996 5.8967 4.4691 4.4647 4.4610 4.4566 3.1009 3.0976 3.0928 3.0895 3.0415 3.0382 3.0334 3.0305 2.7787 2.7659 2.7193 2.7069 1.5967

(ppm)

1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.5

194.1412 149.2977 142.4470 132.2291 127.3680 118.4474 113.1708 101.9326 81.3585 77.2116 37.9070 21.9462

(ppm)

0 20 40 60 80 100 120 140 160 180 200

(8)

Me O

O O

F H

1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0

7.5 ppm

1.63

2.612.632.672.682.962.972.972.973.023.023.033.03

4.334.344.354.35

5.81

6.156.166.196.19

6.606.606.636.64

7.057.077.087.117.277.417.427.437.447.46

3.29 1.02 1.03 0.97 0.99 1.00 1.01 2.05 0.07 2.03

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

21.29

38.69

78.0879.14

102.13

115.28115.56

128.21128.33130.13134.07134.11

146.99

161.73165.01

195.19

(9)

Me O

O O

H F

1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0

7.5 ppm

1.58

2.712.722.762.783.023.033.033.033.083.093.093.09

4.424.434.434.444.444.45

5.955.955.985.995.99

6.556.566.596.607.017.027.037.047.077.087.357.357.367.377.387.39

4.30 1.00 1.00 0.97 1.77 0.97 2.04 1.93

20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190

200 ppm

21.08

36.90

76.19

80.21

101.74

114.21114.50

125.32127.71127.83132.13

148.85

157.43

161.10

193.39

(10)

Me O

O O

H Me

O 2 N

2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5

8.0 ppm

1.64

2.10

2.622.632.672.692.962.962.972.973.023.023.033.03

4.284.294.30

5.83

6.056.066.06

7.637.66

8.238.26

3.44 3.21 1.04 1.06 1.00 1.05 1.05 2.26 2.34

30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190

200 ppm

17.6420.02

38.12

79.9680.75

100.85

123.66127.21128.33

145.11

148.56

156.93

194.34

(11)

Me O

O O

H NO 2

Me

.

2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5

8.0 ppm

1.61

1.89

2.732.752.792.81

3.073.13

4.48

5.83

6.10

7.547.57

8.218.24

3.71 3.11 1.09 1.06 1.00 1.05 1.25 2.09 2.29

30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180

190 ppm

18.2220.77

37.66

79.02

82.11

101.76

123.60125.56127.49

144.44

152.61

159.83

193.82

(12)
(13)
(14)
(15)
(16)
(17)
(18)

30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180

190 ppm

21.9322.8422.9624.22

38.02

43.75

75.58

80.36

103.43

125.98

150.40

194.98

(19)

ppm

0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5

7.0 ppm

0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0

H

H

O

O M e O

H

H

ep i -1 5a

(20)
(21)
(22)
(23)
(24)
(25)
(26)
(27)
(28)
(29)
(30)
(31)
(32)
(33)
(34)
(35)
(36)
(37)

epi-17e

(38)
(39)
(40)
(41)
(42)
(43)

ppm

1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5

8.0 ppm

1

2

3

4

5

6

7

8

H

H

H

TsN

O

Me O

Ts N

H Ph Ph

H

H

H H

H 23a 18a

epi-18a

(44)
(45)

ppm

1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5

8.0 ppm

1

2

3

4

5

6

7

8

H Me

H

H T s N H

O

M e O

T s N

H H P h

P h

H

H H

ep i -2 3a epi-18a

(46)
(47)
(48)
(49)
(50)
(51)
(52)
(53)
(54)

1 H and 13 C NMR Spectra CHAPTER 3.1

(55)
(56)
(57)
(58)
(59)
(60)
(61)
(62)
(63)
(64)
(65)
(66)
(67)
(68)
(69)
(70)
(71)
(72)
(73)
(74)
(75)
(76)

HPLC data for 177a: IC-0.8ml/min-15% isopropanol-45 min

(77)

HPLC data for 177b: IC-0.8ml/min-15% isopropanol-45 min

(78)

HPLC data for 177d: IC-0.8ml/min-10% isopropanol-60 min

(79)

HPLC data for 177e: IC-0.8ml/min-15% isopropanol-45 min

(80)

HPLC data for 177i: IC-0.8ml/min-15% isopropanol-45 min

(81)

HPLC data for 177j: IC-0.8ml/min-17% isopropanol-60 min

(82)

1 H and 13 C NMR Spectra CHAPTER 3.2

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(86)
(87)
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(89)
(90)
(91)
(92)
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(102)

Referencias

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