DOMINO REACTIONS IN LIBRARY SYNTHESIS - Diversity-Oriented Synthesis - page 152

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SCHEME 5.9 One-pot four-component synthesis of pyrrolo[3,4- b ]pyridin-5-ones 23 .

TABLE 5.6 Pyrrolo[3,4- b ]pyridin-5-ones 23
Entry R 1 R 2 R 3 R 4 Yield (%) a

1 n -Hex (CH 2 ) 5 CO 2 Me Bn CO 2 Et 23i ,50

2 4-MeO-Ph n -Bu Bn CO 2 Et 23j ,55

3 n -Hex ( R )-CH(PhCH 2 )CO 2 Me Bn CO 2 Et 23k ,54

4 n -Hex ( S )-CH(PhCH 2 )CO 2 Me Bn CO 2 Et 23l ,48

5 n -Hex ( S )-CH(CH 2 CO 2 Me)CO 2 Me Bn CO 2 Et 23m ,40

6 4-Cl-Ph n -Bu Bn 4-NO 2 -Ph 23n ,32

7 n -Hex (CH 2 ) 5 CO 2 Me Bn 4-NO 2 -Ph 23o ,75

8 n -Hex n -Bu Bn 4-NO 2 -Ph 23p ,71

9 n -Hex 2-[3 ,4 -OMe) 2 ]Ph(CH 2 ) 2 Bn 4-NO 2 -Ph 23q ,70

10 Ph n -Bu Bn 4-NO 2 -Ph 23r ,70

11 Ph (CH 2 ) 5 CO 2 Me Bn 4-NO 2 -Ph 23s ,35

12 n -Hex (CH 2 ) 5 CO 2 Me Bn 4-OMe-Ph 23t ,65

a Isolated yields.

SCHEME 5.10 Synthesis of tetracyclic pyrimidines.