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. Author manuscript; available in PMC: 2013 Dec 24.
Published in final edited form as: Org Lett. 2009 Feb 19;11(4):10.1021/ol802755z. doi: 10.1021/ol802755z

Table 1.

Angularly Substituted Indenoisoquinolines

graphic file with name nihms-91539-f0006.jpg
entry R1 R2 R3 prdtb yieldc (%)
1 H OMe H 5a 75 (71)d
2 H Me H 5b 69
3 H H H 5c 67 (17)d
4 H Cl H 5d 49 (11)d
5 H COOMe H 5e 38
6 H OMe OMe 5f 77
7 H -OCH2CH2O- 5ge 71
8 OMe OMe OMe 5h 64
9 H NMe2 H 5i 59
10 thiophene-2-yl 5j 74

aMethod A: was used for all the entries: (i) CuCl (20%), MeCN/CH2Cl2, 45 °C, 6 h, imine : acyl chloride : stannane = 1.0 : 1.2 : 1.5 (mol); (ii) aqueous KF, filtration, evaporation; (iii) Pd(OAc)2 (5%), NaOAc (1.0 equiv), DMF, 120 °C, 24 h.

b

With one exception, a single diastereomer was isolated.

c

Isolated yield of heterocycles 5 obtained via Method A calculated per imine as the limiting reagent.

d

Yield of heterocycle 5 obtained by Method B is given in parentheses. Method B: same as Method A, but substituting Na2CO3 (1.0 equiv)/n-Bu4NCl (1.0 equiv) for NaOAc.

e

Product was isolated as a 4 : 1 mixture of diastereomers (by 1H NMR), the major diastereomer is shown.