88
1 Supplementary Information for Tandem Catalytic Oxidative Deacetylation of Acetoacetic Esters and Hetero Aromatic Cyclizations Yeming Ju, a,b Di Miao, a,b Ruiyang Yu a,b and Sangho Koo* a,b,c a School of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai, 200237, China, b Department of Energy and Biotechnology, c Department of Chemistry, Myong Ji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do, 449-728, Korea. [email protected] Prof. Sangho Koo, phone: +82-31-330-6185, fax: +82-31-335-7248 [ 1 H/ 13 C NMR spectra for the new compounds] Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is © The Royal Society of Chemistry 2014

Supplementary Information for Tandem Catalytic … · Tandem Catalytic Oxidative Deacetylation of Acetoacetic Esters and Hetero ... aSchool of Pharmacy, ... OEt O 29 EtO 2C OH OEt

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1

Supplementary Information for

Tandem Catalytic Oxidative Deacetylation of

Acetoacetic Esters and Hetero Aromatic Cyclizations

Yeming Ju,a,b Di Miao,a,b Ruiyang Yua,b and Sangho Koo*a,b,c

aSchool of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai,

200237, China, bDepartment of Energy and Biotechnology, cDepartment of Chemistry, Myong Ji

University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do, 449-728, Korea.

[email protected]

Prof. Sangho Koo, phone: +82-31-330-6185, fax: +82-31-335-7248

[1H/13C NMR spectra for the new compounds]

Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2014

2

EtO

OO

O1

3

EtO

O

O

O

2

4

EtO

OO

O

OH

3

5

EtO

OO

O

OH

3

6

OO

O 4

OO

OH

7

OO

O 4

OO

OH

8

OO

O O

OH

5

9

OO

O O

OH

5

10

O

O

O

6

11

O

O

O

6

12

OEtO2C7

13

OEtO2C7

14

SEtO2C8

15

SEtO2C8

16

NH

CO2Et

9

17

N CO2EtBn 10

18

N CO2EtBn 10

19

N CO2EtBu 11

20

N CO2EtBu 11

21

N

CO2Et

(CH2)3OH

12

22

N

CO2Et

(CH2)3OH

12

23

N

CO2Et

CH2C CH

13

24

N

CO2Et

CH2C CH

13

25

N

CO2Et

14

26

N

CO2Et

14

27

N

CO2Et

I

15

28

N

CO2Et

I

15

29

N

CO2Et

OMe

16

30

N

CO2Et

OMe

16

31

N

CO2Et CO2Et

17

32

N

CO2Et CO2Et

17

33

N

CO2Et

N

EtO2C18

34

N

CO2Et

N

EtO2C18

35

N

CO2Et

CH2OH19

36

N

CO2Et

CH2OH19

37

N

CO2Et

NHBoc20

38

N

CO2Et

NHBoc20

39

N NEtO2C

21

40

N NEtO2C

21

41

N

OO

22

42

N

OO

22

43

NH

N

O

23

44

NH

N

O

23

45

EtO

O

O

NO2

24

EtO

O

OH

NO2

46

EtO

O

O

NO2

24

EtO

O

OH

NO2

47

EtOO

O NO2

25

48

EtOO

O NO2

25

49

EtO

O

O

NO2OH

26

50

EtO

O

O

NO2OH

26

51

NH

CO2Et

27

52

NH

CO2Et

27

53

EtO

O

O

NO2

28CO2Et

EtO

O

OH

NO2

CO2Et

54

EtO

O

O

NO2

28CO2Et

EtO

O

OH

NO2

CO2Et

55

NO2

EtO2CO

OEt

O29

NO2

EtO2COH

OEt

O

56

NO2

EtO2CO

OEt

O29

NO2

EtO2COH

OEt

O

57

NH

CO2EtEtO2C

30

58

NH

CO2EtEtO2C

30

59

NO2

O

OEt

O

Cl

31NO2

HO

OEt

O

Cl

60

NO2

O

OEt

O

Cl

31NO2

HO

OEt

O

Cl

61

Cl

NO2

OOEt

O32

Cl

NO2

OHOEt

O

62

Cl

NO2

OOEt

O32

Cl

NO2

OHOEt

O

63

NO2

O

OEt

O33 NO2

OEt

O

HO

64

NO2

O

OEt

O33 NO2

OEt

O

HO

65

NO2

OEt

O

O

34 NO2

OEt

O

OH

66

NO2

OEt

O

O

34 NO2

OEt

O

OH

67

NH

CO2Et

35

68

NH

CO2Et

35

69

NO2

OEt

O

OOMe

36 NO2

OEt

O

HOOMe

70

NO2

OEt

O

OOMe

36 NO2

OEt

O

HOOMe

71

NO2

OEt

O

OMe

O

37

72

NO2

OEt

O

OMe

O

37

73

NH

MeOCO2Et

38

74

NH

MeOCO2Et

38

75

OMeMeO

NO2

O

OEt

O39

76

OMeMeO

NO2

O

OEt

O39

77

OMeMeO

NO2

OOEt

O40

OMeMeO

NO2

OEt

O

O

41

HO

78

OMeMeO

NO2

OOEt

O40

OMeMeO

NO2

OEt

O

O

41

HO

79

NHMeO

MeOCO2Et

42

80

NHMeO

MeOCO2Et

42

81

NO2

OEt

O

OO O

43NO2

OEt

O

OO HO

82

NO2

OEt

O

OO O

43NO2

OEt

O

OO HO

83

NO2

OOEt

O

OO

44NO2

OEt

O

OO O

45

HO

84

NO2

OOEt

O

OO

44NO2

OEt

O

OO O

45

HO

85

NH

O

OCO2Et

46

86

NH

O

OCO2Et

46

87

N CO2Et

EtO2C

47

88

N CO2Et

EtO2C

47