Abstract
Regioisomeric hexahydrofuro[3,4-b]carbazol-1-ones, hexahydropyrrolo[3,4-b]carbazol-1-ones, hexahydrofuro[3,4-b]carbazol-3-ones and hexahydropyrrolo[3,4-b]carbazol-3-ones were synthesized
in 59% to 62% yields by domino Wittig Diels-Alder
reactions from indole-3-carboxaldehyde and indole-2-carboxaldehyde
and Wittig reagents. Further the corresponding carbazolelactones
and carbazolelactams were obtained by oxidation with DDQ.
Key words
domino Wittig - Diels-Alder - furocarbazoles - pyrrolocarbazoles
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General Procedure
for the Tandem Wittig-Diels-Alder Reaction for
Preparation of Tetrahydrocarbazole Lactones (5a,b/10a,b)
and Tetrahydrocarbazole Lactams (5c,d/10c,d): A solution
of indole carboxaldehyde 1/7 (1 mmol) and phosphorane 2a-d (1.5 mmol) in diphenyl ether (10 mL)
was refluxed under nitrogen atmosphere for 2-8 h. The crude
mixture was subjected to column chromatography over silica gel and
diphenyl ether was removed using hexanes as eluent. Further elution
with
30-40% EtOAc and hexanes afforded
the corresponding
γ-lactones 5a,b/10a,b and γ-lactams 5c,d/10c,d.
General
Procedure for Aromatization Using DDQ: A mixture of tetrahydrocarbazoles 5a-d/10a-d (1
mmol) and DDQ (3 mmol) in dioxane (10 mL) was refluxed for 8 h.
The reaction mixture was allowed to cool to ambient temperature and
filtered. The filtrate was then concentrated under reduced pressure.
The resulting residue was dissolved in EtOAc (20 mL) and washed
with 2 N NaOH (20 mL) and H2O (20 mL). The organic phase
was dried over anhyd Na2SO4 and concentrated
under reduced pressure. The resulting residue on purification using
flash chromatography with hexanes-EtOAc (70:30) gave the
oxidized products 6a-d/11a-d.
3,5-Dihydro-1
H
-furo[3,4-
b
]carbazol-1-one
(6a): ¹H NMR (300 MHz, DMSO): δ = 5.46
(s, 2 H), 7.21 (t, J = 7.8 Hz,
1 H), 7.49 (t, J = 7.8 Hz, 1
H), 7.53 (d, J = 8.1 Hz, 1 H),
7.62 (s, 1 H), 8.30 (d, J = 7.8
Hz, 1 H), 8.66 (s, 1 H), 11.78 (s, 1 H). ¹³C
NMR (300 MHz, DMSO): δ = 69.85, 104.29, 111.83, 116.03,
118.12, 120.10, 121.47, 122.56, 124.50, 127.28, 141.27, 144.40,
144.85, 171.69. HRMS: m/z [M + Na] calcd for
C14H9O2N: 246.0531; found: 246.0524.
