130
ORGANIC SYNTHESIS—1995
T.F.
Aromatic Substitutions Forming a New Carbon-Carbon
Bond
Ï.F.I. Friedel-Crafts Type Aromatic Substitution Reactions
I.F.l-l Katritzky, A.R. et al., H, 38, 1813; Sheffer-Dee-Noor, S. and
Ben-Ishai, D., T, 50, 7009; see also: Smith, K. and Pollaud, G.M.,
JCS(Pl), 3519
OH
Ν-"Λ
AcOH, Δ
+
I
N
►
N * ^
R 2 N
R,N
59-72%
I.F.1-2 Vernon, J.M. et al., TL, 35, 7115; Muehldorf, A.V. et al., TL,
35, 8755; Parlow, J.J., T, 50, 3297.
TFA,A
69-83%
I.F.1-3 Gallagher, P.T. et al., TL, 35, 289; Srinivasan, K.V. et al., TL,
35, 2601; Nakatsuka, S. et al., TL, 35, 2699; see also: Niestroj, M. et al.,
CB, 127, 1131.
OMe
C0 2 Et
OMe
Ac 2 0, NaOAc
140°C, 4h
OMe
OAc
OMe
85%
ORGANIC SYNTHESIS—1995
T.F.
Aromatic Substitutions Forming a New Carbon-Carbon
Bond
Ï.F.I. Friedel-Crafts Type Aromatic Substitution Reactions
I.F.l-l Katritzky, A.R. et al., H, 38, 1813; Sheffer-Dee-Noor, S. and
Ben-Ishai, D., T, 50, 7009; see also: Smith, K. and Pollaud, G.M.,
JCS(Pl), 3519
OH
Ν-"Λ
AcOH, Δ
+
I
N
►
N * ^
R 2 N
R,N
59-72%
I.F.1-2 Vernon, J.M. et al., TL, 35, 7115; Muehldorf, A.V. et al., TL,
35, 8755; Parlow, J.J., T, 50, 3297.
TFA,A
69-83%
I.F.1-3 Gallagher, P.T. et al., TL, 35, 289; Srinivasan, K.V. et al., TL,
35, 2601; Nakatsuka, S. et al., TL, 35, 2699; see also: Niestroj, M. et al.,
CB, 127, 1131.
OMe
C0 2 Et
OMe
Ac 2 0, NaOAc
140°C, 4h
OMe
OAc
OMe
85%