Entrya

ArN=O

X

Ar-C(O)C≡CH or

Hetar-C(O)C≡CH

Ar or Het

R

Prod.

Yield (%)

1

1a

4-NO2

19a

H

20

15b

2

1a

4-NO2

19b

OH

21

22c

3

1a

4-NO2

19c

OH

22

32c,d

4

5

1a

1b

4-NO2

4-COOH

19d

19d

OH

OH

23

24

41c

64d,e

6

1b

4-COOH

19e

OH

25

16b,e

7

8

1b

1c

4-COOH

4-CN

19f

19f

H

H

26

27

37e,f

39b

9

10

1d

1i

1i

4-Br

H

H

19g

19g

19g

H

OH

H

28

29

30

37c

38b

17b

11

12

13

1a

1h

1i

4-NO2

2-NO2

H

19h

19h

19h

H

H

H

31

32

33

30b

45b

32b

14

1b

4-COOH

19i

OH

34

50d,e

15

16

17

1a

1i

1j

4-NO2

H

2-COOCH3

19j

19j

19j

OH

H

OH

35

36

37

50c

53b

24c

18

1a

4-NO2

19k

H

38

not isolatedg