References and Notes
<A NAME="RB76311ST-1A">1a</A>
Talapatra SK.
Bose S.
Mallik AK.
Talapatra B.
Tetrahedron
1985,
41:
2765
<A NAME="RB76311ST-1B">1b</A>
Greenlee ML.
Laub JB.
Rouen GP.
DiNinno F.
Hammond ML.
Huber JL.
Sundelof JG.
Hammond GG.
Bioorg. Med. Chem. Lett.
1999,
9:
3225
<A NAME="RB76311ST-1C">1c</A>
Qabaja G.
Jones GB.
Tetrahedron Lett.
2000,
41:
5317
<A NAME="RB76311ST-1D">1d</A>
Zhang X.
Xu J.-K.
Wang J.
Wang N.-L.
Kurihara H.
Kitanaka S.
Yao
X.-S.
J.
Nat. Prod.
2007,
70:
24
<A NAME="RB76311ST-1E">1e</A>
Reddy KS.
Solá L.
Moyano A.
Pericàs MA.
Riera A.
Synthesis
2000,
165
<A NAME="RB76311ST-1F">1f</A>
Liu T.-P.
Liao Y.-X.
Xing C.-H.
Hu Q.-S.
Org. Lett.
2011,
13:
2452
<A NAME="RB76311ST-1G">1g</A>
Silveira CC.
Larghi EL.
Mendes SR.
Bracca ABJ.
Rinaldi F.
Kaufman TS.
Eur.
J. Org. Chem.
2009,
4637
<A NAME="RB76311ST-2A">2a</A>
Bauer I.
Knölker H.-J.
Top.
Curr. Chem.
2011,
1
<A NAME="RB76311ST-2B">2b</A>
Knölker H.-J.
Reddy KR. In The Alkaloids
Vol. 65:
Cordell GA.
Academic
Press;
Amsterdam:
2008.
p.1-430
<A NAME="RB76311ST-2C">2c</A>
Knölker H.-J.
Reddy KR.
Chem.
Rev.
2002,
102:
4303
<A NAME="RB76311ST-3A">3a</A>
Lescot E.
Muzard G.
Markovits J.
Belleney J.
Roques BP.
Le Pecq J.-B.
J. Med. Chem.
1986,
29:
1731
<A NAME="RB76311ST-3B">3b</A>
Woodward RB.
Iacobucci GA.
Hochstein FA.
J. Am. Chem. Soc.
1959,
81:
4434
<A NAME="RB76311ST-4A">4a</A>
Gruner KK.
Hopfmann T.
Mastumoto K.
Jäger A.
Katsuli T.
Knölker H.-J.
Org.
Biomol. Chem.
2011,
9:
2057
<A NAME="RB76311ST-4B">4b</A>
Gruner KK.
Knölker H.-J.
Org.
Biomol. Chem.
2008,
6:
3902
<A NAME="RB76311ST-5">5</A>
Engler TA.
Furness K.
Malhotra S.
Sanchez-Martinez C.
Shih C.
Xie W.
Zhu G.
Zhou X.
Conner S.
Faul MM.
Sullivan KA.
Kolis SP.
Brooks HB.
Patel B.
Schultz RM.
DeHahn TB.
Kirmani K.
Spencer CD.
Watkins SA.
Considine EL.
Dempsey JA.
Ogg CA.
Stamm NB.
Anderson BD.
Campbell RM.
Vasudevan V.
Lytlea ML.
Bioorg.
Med. Chem. Lett.
2003,
13:
2261
<A NAME="RB76311ST-6">6</A>
Gingrich DE.
Yang SX.
Gessner GW.
Angeles TS.
Hudkins RL.
J. Med. Chem.
2005,
48:
3776
<A NAME="RB76311ST-7A">7a</A>
Jeong SH.
Lee JY.
J.
Mater. Chem.
2011,
21:
14604
<A NAME="RB76311ST-7B">7b</A>
Kim SH.
Cho I.
Sim MK.
Park S.
Park SY.
J.
Mater. Chem.
2011,
21:
9139
<A NAME="RB76311ST-8A">8a</A>
Ostroverkhova O.
Moerner WE.
Chem.
Rev.
2004,
104:
3267
<A NAME="RB76311ST-8B">8b</A>
Meerholz K.
Volodin BL.
.
Kippelen B.
Peyghambarian N.
Nature
(London)
1994,
371:
497
<A NAME="RB76311ST-9A">9a</A>
Wakim S.
Bouchard J.
Blouin N.
Michaud A.
Leclerc M.
Org. Lett.
2004,
6:
3413
<A NAME="RB76311ST-9B">9b</A>
Zotti G.
Schiavon G.
Zecchin S.
Morin J.-F.
Leclerc M.
Macromolecules
2002,
35:
2122
<A NAME="RB76311ST-9C">9c</A>
Li Y.
Wu Y.
Gardner S.
Ong BS.
Adv. Mater.
2005,
17:
849
<A NAME="RB76311ST-10A">10a</A>
Blouin N.
Leclerc M.
Acc.
Chem. Res.
2008,
41:
1110
<A NAME="RB76311ST-10B">10b</A>
Grimsdale AC.
Chan KL.
Martin RE.
Jokisz PG.
Holmes AB.
Chem. Rev.
2009,
109:
897
<A NAME="RB76311ST-10C">10c</A>
Amb CM.
Dyer AL.
Reynolds JR.
Chem. Mater.
2011,
23:
397
<A NAME="RB76311ST-11A">11a</A>
Brunner K.
van Dijken A.
Börner H.
Bastiaansen JJAM.
Kiggen NMM.
Langeveld BMW.
J.
Am. Chem. Soc.
2004,
126:
6035
<A NAME="RB76311ST-11B">11b</A>
Ho C.-L.
Chi L.-C.
Hung W.-Y.
Chen W.-J.
Lin Y.-C.
Wu H.
Mondal E.
Zhou G.-J.
Wong K.-T.
Wong W.-Y.
J. Mater. Chem.
2012,
22:
215
<A NAME="RB76311ST-12A">12a</A>
Sonntag M.
Strohriegl P.
Tetrahedron
Lett.
2006,
47:
8313
<A NAME="RB76311ST-12B">12b</A>
Sonntag M.
Strohriegl P.
Tetrahedron
2006,
62:
8103
<A NAME="RB76311ST-13">13</A>
Hudkins RL. inventors; WO 2001014380.
<A NAME="RB76311ST-14A">14a</A>
Singh J,
Hudkins RL,
Mallamo JP,
Underiner TL, and
Tripathy R. inventors; WO 9962523.
<A NAME="RB76311ST-14B">14b</A>
Underiner TL.
Mallamo JP.
Singh J.
J. Org. Chem.
2002,
67:
3235
<A NAME="RB76311ST-15">15</A>
Tripathy R.
Learn KS.
Reddy DR.
Singh MIJ.
Mallamo JP.
Tetrahedron Lett.
2002,
43:
217
<A NAME="RB76311ST-16A">16a</A>
Gingrich DE.
Hudkins RL.
Bioorg. Med. Chem. Lett.
2002,
12:
2829
<A NAME="RB76311ST-16B">16b</A>
Gingrich DE.
Reddy DR.
Iqbal MA.
Singh J.
Aimone LD.
Angeles TS.
Albom M.
Yang S.
Ator MA.
Meyer SL.
Robinson C.
Ruggeri BA.
Dionne CA.
Vaught JL.
Mallamo JP.
Hudkins RL.
J. Med. Chem.
2003,
46:
5375
<A NAME="RB76311ST-17A">17a</A>
Bonnamour J.
Bolm C.
Org.
Lett.
2011,
13:
2012
<A NAME="RB76311ST-17B">17b</A>
Alonso DA.
Nájera C.
Pastor IM.
Yus M.
Chem. Eur.
J.
2010,
16:
5274
<A NAME="RB76311ST-17C">17c</A>
Čerňa I.
Pohl R.
Kleptářová B.
Hocek M.
J. Org. Chem.
2010,
75:
2302
<A NAME="RB76311ST-17D">17d</A>
Sahnoun S.
Messaoudi S.
Brion J.-D.
Alami M.
Org. Biomol. Chem.
2009,
7:
4271
<A NAME="RB76311ST-17E">17e</A>
Storr TE.
Baumann CG.
Thatcher RJ.
De Ornellas S.
Whitwood AC.
Fairlamb IJS.
J. Org. Chem.
2009,
74:
5810
<A NAME="RB76311ST-17F">17f</A>
Cao F.
Shen D.
Zhan H.
Yang L.
Synlett
2011,
1472
<A NAME="RB76311ST-18A">18a</A>
Alberico D.
Scott ME.
Lautens M.
Chem. Rev.
2007,
107:
174
<A NAME="RB76311ST-18B">18b</A>
Bellina F.
Rossi R.
Tetrahedron
2009,
65:
10269
<A NAME="RB76311ST-18C">18c</A>
McGlacken GP.
Bateman LM.
Chem.
Soc. Rev.
2009,
38:
2447
<A NAME="RB76311ST-18D">18d</A>
Ackermann L.
Vicente R.
Kapdi AR.
Angew.
Chem. Int. Ed.
2009,
48:
9792
<A NAME="RB76311ST-18E">18e</A>
Racowski JM.
Ball ND.
Sanford MS.
J. Am. Chem. Soc.
2011,
133:
18022
<A NAME="RB76311ST-18F">18f</A>
Cho SH.
Kim JY.
Kwak J.
Chang S.
Chem. Soc.
Rev.
2011,
40:
5068
<A NAME="RB76311ST-19">19</A>
See Supporting Information.
<A NAME="RB76311ST-20">20</A>
Analytical Data
Compound 4a: CCDC deposition number 854724. Formula: C21H15N1O1.
Unit cell parameters: a = 18.8910
(15), b = 14.7317
(11), c = 5.3252
(3), space group P21212.
Compound 4ab: CCDC deposition number 854725. Formula:
C21H15N1O1. Unit cell
parameters: a = 15.9003
(8), b = 5.4237
(3), c = 17.1149
(8), space group Pna21.
Compound 4d: CCDC deposition number 854726. Formula: C22H17N1O2.
Unit cell parameters: a = 8.3015
(8), b = 9.1172
(9), c = 10.6868
(10), α = 83.461
(2), β = 79.759 (2), γ = 81.777
(2), space group P1.
Compound 6b: CCDC deposition number 854727. Formula: C29H18Cl3N1O2.
Unit cell parameters: a = 9.0516
(13), b = 10.4572
(20), c = 13.2939
(17), α = 100.684
(14), β = 101.200(12), γ = 101.784
(15), space group P1.
<A NAME="RB76311ST-21">21</A>
Wong K.-T.
Chao T.-C.
Chi L.-C.
Chu Y.-Y.
Balaiah A.
Chiu S.-F.
Liu Y.-H.
Wang Y.
Org. Lett.
2006,
8:
5033
<A NAME="RB76311ST-22">22</A>
General Procedure
A
mixture of compound 3a (0.10 g, 0.02 mmol),
anhyd KOAc (0.04 g, 0.04 mmol), TBAB (0.06 g, 0.02 mmol), and Pd(OAc)2 (0.003
g, 5 mol%) in DMF (3.0 mL) was taken in a Schlenk tube
and heated at 140 ˚C for 3 h with continuous stirring.
After completion of the reaction as monitored by TLC, the reaction
mixture was cooled and poured into cold H2O (10 mL).
A solid precipitate was formed, extracted with CHCl3 (3 × 20
mL), and washed with H2O (3 × 20
mL) followed by brine (20 mL) and dried over anhyd Na2SO4. Evaporation
of solvent, and the crude material was purified by column chromatography
over silica gel (100-200 mesh), using 12% EtOAc
in hexanes as eluent to give product 4a in 68% yield.
Compounds 4b-g and 6b were obtained using same procedure.
5-Ethylindeno[1,2-
b
]carbazol-11
(5
H
)-one
(4a)
Yellow solid; mp 181-182 ˚C;
yield 68%. IR (KBr): 2986, 1697, 1570, 1446, 1331, 1111,
931, 742 cm-¹. ¹H
NMR (400 MHz, TMS, CDCl3): δ = 8.39
(s, 1 H), 8.05 (d, 1 H, J = 7.6 Hz),
7.66 (d, 1 H, J = 7.2
Hz), 7.59 (d, 1 H, J = 7.2
Hz), 7.50-7.46 (ddd, 2H, J
1 = 1.2
Hz, J
2 = 7.6
Hz, J
3 = 15.2
Hz), 7.42 (s, 1 H), 7.33-7.27 (m, 3 H), 4.41 (q, 2 H, J = 7.2 Hz), 1.51
(t, 3 H, J = 7.2
Hz). ¹³C NMR (100 MHz, TMS, CDCl3): δ = 193.2,
144.6, 144.1, 142.6, 140.7, 136.3, 134.1, 128.8, 126.4, 126.2, 123.8,
123.1, 120.6, 120.5, 119.9, 118.0, 109.1, 100.7, 37.9, 14.0. LC-MS
(positive mode): m/z = 298 [M + H]+.
Anal. Calcd (%) for C21H15NO: C,
84.82; H, 5.08; N, 4.71. Found: C, 84.65; H, 5.12; N, 4.68.
