Supporting Information

Copper-Catalyzed Oxidative Amination of Methanol to Access Quinazolines

Gandhesiri Satish, Polu Ashok, Laxman Kota and Andivelu Ilangovan*School of Chemistry, Bharathidasan University, Tiruchirappalli – 620 024, India.

Email: ilangovanbdu@yahoo.com

1 Copies of 1H and 13C NMR spectra 2-50

Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2019

11 10 9 8 7 6 5 4 3 2 1 0 ppm

7.187

7.305

7.323

7.330

7.340

7.353

7.372

7.389

7.572

7.591

7.610

7.642

7.660

7.803

7.824

7.828

7.831

7.841

7.870

7.966

7.987

8.186

8.225

8.231

8.252

9.215

3.16

1.10

2.08

2.10

1.03

2.06

1.00

N

N

3a

200 180 160 140 120 100 80 60 40 20 0 ppm

76.74

77.06

77.38

120.37

123.94

127.58

128.10

128.98

129.86

133.70

135.83

139.99

151.04

154.72

162.14

N

N

3a

11 10 9 8 7 6 5 4 3 2 1 0 ppm

7.290

7.638

7.657

7.677

7.734

7.752

7.772

7.952

7.970

7.998

8.017

8.056

8.096

8.123

8.257

8.277

8.322

8.362

8.386

8.626

9.345

1.07

1.08

2.09

2.10

3.09

1.01

1.00

N

N

NO2

3b

200 180 160 140 120 100 80 60 40 20 0 ppm

76.75

77.07

77.38

121.89

123.05

123.39

123.73

123.98

127.96

129.17

130.02

133.97

134.12

136.93

137.56

148.77

151.22

154.69

161.05

N

N

NO2

3b

11 10 9 8 7 6 5 4 3 2 1 0 ppm

7.292

7.434

7.454

7.671

7.689

7.705

7.724

7.905

7.919

7.941

7.957

8.072

8.093

8.235

8.273

8.319

8.340

9.313

2.12

3.26

2.17

1.05

1.07

1.08

1.00

N

N

Cl

3c

200 180 160 140 120 100 80 60 40 20 0 ppm

76.72

77.04

77.36

120.95

123.04

123.81

127.65

129.13

129.21

129.24

133.74

134.34

135.64

138.42

151.16

154.77

161.76

N

N

Cl

3c

N

N

OMe

3d

200 180 160 140 120 100 80 60 40 20 0 ppm

55.38

76.82

77.13

77.45

114.39

117.83

122.92

123.91

127.33

128.55

128.88

129.71

133.50

139.55

150.94

154.72

161.06

162.33

N

N

OMe

3d

11 10 9 8 7 6 5 4 3 2 1 0 ppm

3.891

3.910

6.895

7.290

7.602

7.606

7.718

7.756

7.821

7.840

7.979

7.999

8.136

8.174

8.252

8.272

9.225

9.19

2.06

1.04

1.04

1.08

1.09

1.04

1.04

1.00

N

N

OMeOMeMeO

3e

200 180 160 140 120 100 80 60 40 20 0 ppm

56.17

61.00

76.85

77.17

77.49

105.20

119.48

122.90

123.88

127.43

128.94

131.32

133.60

139.74

139.91

151.01

153.45

154.67

161.92

N

N

OMeOMeMeO

3e

11 10 9 8 7 6 5 4 3 2 1 0 ppm

7.290

7.545

7.564

7.583

7.596

7.617

7.634

7.650

7.669

7.688

7.896

7.906

7.918

7.939

7.972

7.989

8.010

8.077

8.098

8.321

8.342

8.386

8.407

9.131

9.169

9.374

2.07

1.08

1.05

3.10

2.08

1.02

1.02

1.04

1.02

1.00

N

N

3f

200 180 160 140 120 100 80 60 40 20 0 ppm

76.76

77.08

77.40

123.08

123.19

123.81

123.97

124.80

125.56

126.28

126.82

127.62

128.74

129.04

130.15

131.74

133.51

133.69

133.78

136.99

151.14

154.87

162.00

N

N

3f

N

N

3g

200 180 160 140 120 100 80 60 40 20 0 ppm

76.82

77.14

77.46

123.01

124.94

125.07

125.43

125.75

126.93

127.16

128.53

128.72

128.77

129.31

130.81

131.16

133.33

135.81

150.17

154.54

164.47

N

N

3g

11 10 9 8 7 6 5 4 3 2 1 0 ppm

7.005

7.014

7.026

7.261

7.268

7.314

7.326

7.515

7.533

7.554

7.571

7.759

7.779

7.797

7.932

7.953

8.107

8.129

8.305

8.343

9.180

1.05

2.08

2.09

1.09

1.07

1.06

1.03

1.00

N

N

3h

S

200 180 160 140 120 100 80 60 40 20 0 ppm

76.90

77.22

77.54

119.23

122.71

123.73

127.37

127.84

128.22

128.86

130.65

132.35

133.52

141.33

150.94

154.62

161.57

N

N

3h

S

11 10 9 8 7 6 5 4 3 2 1 0 ppm

6.949

6.988

7.079

7.106

7.118

7.145

7.274

7.292

7.309

7.338

7.356

7.375

7.391

7.428

7.478

7.497

7.566

7.584

7.604

7.808

7.828

7.846

7.984

8.006

8.016

8.044

8.053

8.081

8.146

8.167

9.249

1.02

1.04

1.15

3.18

2.08

1.12

1.06

2.01

0.99

1.00

N

N

3i

200 180 160 140 120 100 80 60 40 20 0 ppm

76.87

77.19

77.51

122.83

123.78

124.04

127.14

127.39

127.80

128.82

128.86

128.93

133.49

136.43

139.65

140.17

151.01

154.76

161.95

N

N

3i

11 10 9 8 7 6 5 4 3 2 1 0 ppm

7.290

7.426

7.444

7.469

7.487

7.504

7.755

7.773

7.815

7.853

7.932

7.954

7.971

7.975

7.994

7.997

8.303

8.341

8.471

9.307

3.08

3.04

2.07

1.00

1.01

1.00

N

NBr

3j

200 180 160 140 120 100 80 60 40 20 0 ppm

76.82

77.14

77.45

119.54

121.25

123.88

126.26

127.37

128.20

128.98

130.06

130.76

135.49

136.99

140.59

149.67

154.94

161.09

N

NBr

3j

N

NBr

Br 3k

N

NBr

Br 3k

11 10 9 8 7 6 5 4 3 2 1 0 ppm

2.954

7.618

7.637

7.656

7.863

7.883

7.901

8.016

8.037

8.074

8.095

9.171

3.09

1.05

1.07

1.01

1.05

1.00

N

N

CH3

3l

200 180 160 140 120 100 80 60 40 20 0 ppm

21.73

76.81

77.13

77.45

124.40

124.99

127.59

128.88

133.69

149.41

154.40

168.25

N

N

CH3

3l

N

N

CH3Br

Br3m

N

N

CH3Br

Br3m

11 10 9 8 7 6 5 4 3 2 1 0 ppm

1.438

1.455

1.467

1.473

3.295

3.306

3.313

3.331

7.616

7.635

7.840

7.858

7.877

8.018

8.039

8.095

8.116

9.224

3.19

1.97

1.11

1.10

2.22

1.00

N

N

CH3

3n

200 180 160 140 120 100 80 60 40 20 0 ppm

12.61

27.60

76.85

77.17

77.49

123.62

124.46

127.46

128.99

133.42

149.60

154.53

172.35

N

N

CH3

3n

N

N

3o

N

N

3o

N

N

3p

Cl

N

N

3p

Cl

N

N

3q

O2N

N

N

3q

O2N

N

NO

O

CH3

3r

N

NO

O

CH3

3r

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.5f1 (ppm)

2.8

3

2.9

70

.99

2.0

13

.10

1.9

9

2.8

5

7.1

97

.30

7.3

17

.31

7.3

37

.35

7.3

77

.38

7.3

97

.49

7.4

97

.51

7.5

27

.53

7.6

47

.66

7.6

67

.75

7.7

57

.77

7.7

77

.79

7.7

97

.81

7.8

57

.87

7.8

98

.15

8.1

88

.19

8.2

0

N

N

CH33s

200 180 160 140 120 100 80 60 40 20 0 ppm

26.61

76.75

77.07

77.39

120.69

120.95

123.88

126.59

128.04

128.23

128.92

129.67

133.60

135.97

139.65

151.37

162.19

163.85

N

N

CH33s

N

NCH3

3t

200 180 160 140 120 100 80 60 40 20 0 ppm

13.15

33.23

76.75

77.07

77.38

120.88

121.19

123.86

126.54

128.03

128.39

128.91

129.61

133.47

136.05

139.51

151.43

162.19

167.95

N

NCH3

3t

11 10 9 8 7 6 5 4 3 2 1 0 ppm

1.095

1.113

1.131

2.018

2.037

2.056

2.066

2.075

3.122

3.142

3.161

7.290

7.406

7.423

7.442

7.460

7.478

7.572

7.592

7.610

7.736

7.754

7.837

7.857

7.876

7.906

7.945

7.996

8.017

8.259

8.286

8.297

3.15

2.10

2.04

3.05

1.02

2.00

1.01

1.05

0.97

2.00

N

N

CH33u

200 180 160 140 120 100 80 60 40 20 0 ppm

14.16

22.38

42.06

76.77

77.08

77.40

120.91

121.17

123.84

126.50

128.01

128.44

128.90

129.58

133.40

136.06

139.43

151.42

162.07

167.02

N

N

CH33u

N

NCH3

3v

200 180 160 140 120 100 80 60 40 20 0 ppm

14.10

22.82

31.19

39.92

76.75

77.07

77.39

120.93

121.15

123.84

126.48

128.02

128.45

128.90

129.58

133.39

136.07

139.42

151.46

162.06

167.25

N

NCH3

3v

4.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.5 ppm

7.139

7.271

7.289

7.307

7.327

7.346

7.364

7.397

7.407

7.415

7.433

7.438

7.444

7.462

7.478

7.635

7.653

7.712

7.732

7.750

7.802

7.840

7.957

7.978

8.129

8.149

8.305

8.343

8.607

8.626

1.08

2.04

4.10

2.03

1.10

1.00

1.06

1.02

1.01

2.00

N

N

Ph3w

200 180 160 140 120 100 80 60 40 20 0 ppm

76.79

77.10

77.42

120.91

121.67

123.86

126.87

128.11

128.65

128.97

129.32

129.65

130.46

133.50

136.12

138.57

139.46

152.02

160.15

161.89

N

N

Ph3w

N

NOH

3y

N

NOH

3y

N

N

D3z

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

76

.84

77

.16

77

.48

12

0.4

31

23

.11

12

3.9

31

27

.54

12

8.1

21

29

.00

12

9.1

01

29

.85

13

3.6

31

35

.89

13

9.8

8

15

1.1

61

54

.18

15

4.4

91

54

.84

16

2.0

8

153.0154.0155.0f1 (ppm)

15

4.1

8

15

4.4

9

15

4.8

4

N

N

D3z