Friedel-crafts czocwdhlated - 1-Oxoindanes ikom Aromatic ~Diawhon~ Compounds

and Aldehydes

'0 e c Y + 1 ’ 2

a!?= 1: R R

1 2 3

7339

7340

+ R’CHI

M = h3gmoEt2); AI%

R1=&~OMc R2=OE&,Me R3=H,Ar.CH=CH-Ar

Table. lZl&rophilic bis-alkylation of annatic wyl compounds.

Entry R’ R2 R3 Yield(%) !S&ctivity(%) Method

a H OEt H 72 (93) A

b Me ,t 11 78 (92) ”

c OMe II 11 65 (85)(1 ”

d H Me H 66 (87) ”

e II OEt w5 72 (88) B

f II II PQWQ 58 (87) ”

8 II

h OMe

i H

1 OMe

m H a-time: isrryinute~. bRea&mtimc lhour

P-OMew 70

w5 82

C!H=CH-C+$-I5 63 11 68

5 48

(89) ”

(90) w

(78) ”

(n)b St

(78)b ”

L ‘!

+ R’ar,

6

0

*

c 1

R I

6

7342

This work was sapported by the (lsui@o Nazimdc ddlc Iticabc (CN.R, Roma), Progetto

AnaliaaoulimicaRnee~lIandbytbe~MinistKo~~edBlla~SciaJtiEIcae

Tccnologica (M.U.R.S.T.).

1.

2.

3.

4.

5.

6.

7.

8.

9.

10.

11.

12.

13.

14.

a) Casnati, G.; Casiragbi, G.; Pochhi, A; htori, 6.; Ungaro, R Pwv A&. Ch. l!NU, 55.1677; b)

Sartori, 0.; Casnad, G.; Bigi, I?; P&hi, 0. J. Org. Chem. 1990,55,4371; c) !hrtoti, 0.; Maggi, R,

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Casiraghi, G.; Casnari. G.; Chmia, m; Sattori, G.; Ungaro, R J. Chem. Sot. Perkin Tmns. f, 1974,

2077.

fhhghi, G.; Casnati, G.; C!mia, M.; Pochhi, A.; Fbglh, G.; Sartori. G.; Uqaro, R J. Chem. Sot. Perkin Trans. I, 197S. 3 18

cbmpounds 4 wcxc plwioluly pspmd by cyd~~0ll of the eaarerponding 3-arylpmpiolljc acid

derivatives: a) Setha, S. “Qdiacy~ iu Olah, G.A. Friedel-C@s and R&ted Renctions; In&m Publishers: New York, 1964, VoL III, Part 2, pp 911-1002; b) Remrsrylat V.;

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Horneyer, A.H.; Jones, M. ikd., 1941.63.2252; c) Org. Synth. Coll. VoL IV, 1963,415.

Trost, B.M.; Fleming, L Comprehensive Orgunic Sym%e& Scmmelhd, M.F. Ed.; kqaman Press:

Oxford, 1991, VoL 4, p. 230 ad n&rcnces the&n.

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1990, pp 209-214.

(Received in UK 10 August 1993; accepted 10 September 1993)