2230
A. G. Neo et al.
LETTER
Torroba, T. J. Heterocycl. Chem. 2000, 37, 1501. (i) Bossio,
R.; Marcaccini, S.; Pepino, R.; Marcos, C. F. J. Chem. Educ.
2000, 77, 382. (j) Bossio, R.; Marcos, C. F.; Marcaccini, S.;
Pepino, R. Synthesis 1997, 1389. (k) Bossio, R.; Marcos, C.
F.; Marcaccini, S.; Pepino, R. Heterocycles 1997, 45, 1589.
(l) Bossio, R.; Marcos, C. F.; Marcaccini, S.; Pepino, R.
Tetrahedron Lett. 1997, 38, 2519.
Acknowledgment
For financial support we thank the Instituto de Salud Carlos III
(PI081234), Junta de Extremadura and FEDER.
Supporting Information for this article is available online at
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(15) (a) Díaz-Álvarez, J.; Carrillo, R. M.; Garrido, L.; Neo, A. G.;
Delgado, J.; Jover, A.; Marcaccini, S.; Marcos, C. F.; Book
of Abstracts, 16th European Symposium on Organic
Chemistry (ESOC 2009), Prague, Czech Republic, 2009;
170; ISBN: 978-80-02-02160-5. (b) Díaz-Álvarez, J.; Neo,
A. G.; Carrillo, R. M.; Garrido, L.; Delgado, J.; Marcos, C.
F.; Book of Abstracts, 1st Portuguese Young Chemist
Meeting (1stPYCheM), Lisbon, Portugal, 2008; 79.
Primary Data for this article are available online at
cited using the following DOI:DyarmaPtirDayr
1
Chemyrtsi
(16) General procedure for the cycloaddition of formyl-
chromones and isocyanides: Isocyanide 2 (2.5 mmol) was
added to a solution of formyl chromone 1 (5 mmol) in
anhydrous THF (5 mL). The resulting solution was heated at
reflux under N2 for 5–8 h, and cooled to 0 °C. The precipitate
was collected by filtration. An additional amount of product
was recovered by concentration of the filtrate and
References and Notes
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(17) Representative data: 7-Methyl-1-[1-(6-methyl-4-oxo-4H-
1-benzopyran-3-yl)-meth-(Z)-ylidene]-3-[(Z)-pentylimino]-
1,3-dihydrofuro[3,4-b][1]benzopyran-9-one (3f): Yield:
61%; yellow solid; mp 230–231 °C; IR: 1676, 1651, 1618,
1484, 816 cm–1; 1H NMR (400 MHz, CDCl3): δ = 8.69 (br s,
1 H, CH-2′), 8.09 (br s, 1 H, CH-8), 8.05 (br s, 1 H, CH-5′),
7.56 (d, J = 8.5 Hz, 1 H, CH-5), 7.53 (dd, J = 8.5, 2.1 Hz,
1 H, CH-6), 7.42 (dd, J = 8.5, 2.1 Hz, 1 H, CH-7′), 7.34 (d,
J = 8.5 Hz, 1 H, CH-8′), 7.13 (br s, 1 H, CH-9′), 3.72 [t,
J = 7.0 Hz, 2 H, CH2(CH2)3CH3], 2.48 (s, 3 H, C7-CH3),
2.44 (s, 3 H, C6′-CH3), 1.82 [m, 2 H, CH2CH2(CH2)2CH3],
1.47 [m, 2 H, -(CH2)2CH2CH2CH3], 1.43 [m, 2 H, -
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(CH2)3CH2CH3], 0.95 [t, J = 7.2 Hz, 3 H, -(CH2)4CH3]; 13
NMR (100 MHz, CDCl3): δ = 174.9 [C(4′)=O], 172.3
C
[C(9)=O], 155.8 (CH-2′), 154.5 (C-4a), 154.0 (C-8a′), 152.6
(C-3a), 148.2 (C-3), 143.9 (C-1), 136.3 (C-7), 135.8 (CH-6),
135.3 (C-6′), 134.8 (CH-7′), 125.8 (CH-8), 125.7 (CH-5′),
124.3 (C-8a), 123.2 (C-4a′), 119.9 (C-9a), 119.2 (C-3′),
118.6 (CH-5), 117.8 (CH-8′), 97.1 (CH-9′), 49.1 [-CH2-
(CH2)3CH3], 30.2 [-CH2CH2(CH2)2CH3], 29.7 [-
(CH2)2CH2CH2CH3], 22.5 [-(CH2)3CH2CH3], 20.9
(2 × ArCH3), 14.0 [-(CH2)4CH3]; MS (EI): m/z (%) = 455
(73) [M+], 412 (56), 398 (60), 384 (54), 371 (100), 222 (23),
134 (41); HRMS (EI): m/z calcd for C28H25NO5: 455.1733;
found: 455.1741.
(18) CCDC 886508 contains the supplementary crystallographic
data for compound 3a can be obtained free of charge from
The Cambridge Crystallographic Data Centre via
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Synlett 2012, 23, 2227–2230
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