Transformations of 4-oxo-4H-chromene-3-carbaldehyde under the action of Fe(CO)5

Ambartsumyan, A. A.; Vasil’eva, T. T.; Chakhovskaya, O. V.; Mysova, N. E.; Тuskaev, Vladislav А.; Khrustalev, Victor N.; Кочетков, К. А.

doi:10.1134/s1070428012030207

Cited by 7 publications

(9 citation statements)

References 15 publications

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“…Interestingly, 3-methyl-4H-chromen-4-one (33) 13 was formed in low yield (4e9%) as byproduct from the reaction of the salicylaldehyde 6 with 1,3-thiazolidine-4-carboxylic acid (18). This observation reinforces the mechanism proposal for the synthesis of chromeno-pyrrolo[1,2-c]thiazole 26 since 4H-chromen-4-one 33 derives from the postulated intermediate 27 (Scheme 6).…”

Section: Resultssupporting

confidence: 72%

Reactivity of sarcosine and 1,3-thiazolidine-4-carboxylic acid towards salicylaldehyde-derived alkynes and allenes

2013

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The reaction of sarcosine and 1,3-thiazolidine-4-carboxylic acid with salicylaldehyde-derived alkynes and allenes opened the way to new chromeno[4,3-b]pyrrole and chromeno[2,3-b]pyrrole derivatives. Tetrahydro-chromeno[4,3-b]pyrroles were obtained from the reaction of these secondary amino acids with O-propargylsalicylaldehyde. Interestingly, sarcosine reacted with ethyl 4-(2-formylphenoxy)but-2ynoate to give a monocyclic pyrrole resulting from rearrangement of the initially formed 1,3-dipolar cycloadduct. Decarboxylative condensation of ethyl 4-(2-formylphenoxy)but-2-ynoate with 1,3thiazolidine-4-carboxylic acid afforded in a stereoselective fashion the expected chromeno-pyrrolo [1,2-c]thiazole, which structure was unambiguously established by X-ray crystallography. However, the 1H,3H-pyrrolo[1,2-c]thiazole resulting from the opening of the pyran ring was also isolated. The reaction with O-buta-2,3-dienyl salicylaldehyde afforded 3-methylene-hexahydrochromeno[4,3-b]pyrrole. O-Allenyl salicylaldehyde reacted with sarcosine and 1,3-thiazolidine-4-carboxylic acid to give a new type of chromeno-pyrroles. A mechanism proposal for the synthesis of these chromeno[2,3-b]pyrroles has been presented.

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Section: Resultssupporting

confidence: 72%

Reactivity of sarcosine and 1,3-thiazolidine-4-carboxylic acid towards salicylaldehyde-derived alkynes and allenes

2013

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“…The angle subtended at C12 by the C-C bonds (C1-C12-C20) is 114.87 (2)°. The olefinic bond length [C1-C15 = 1.324 (4) Å] is close to the values found in known chromanone systems (Ambartsumyan et al, 2012). Some examples of bischromanone structures are known (Dean & Murray, 1975)…”

Section: S1 Commentsupporting

confidence: 77%

“…For backgound to bis-chromanones, see: Dean & Murray (1975); Santhosh & Balasubramanian (1991); Panja et al (2009). For related structures, see: Ambartsumyan et al (2012); Nyburg et al (1986); Li et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

rac-7-Methyl-3-[(7-methyl-4-oxochroman-3-yl)methyl]-4H-chromen-4-one

et al. 2013

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Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.004 Å; R factor = 0.059; wR factor = 0.180; data-to-parameter ratio = 17.6.In the racemic title compound, C 21 H 18 O 4 , the chromone ring is essentially planar [maximum deviation from the least-squares plane = 0.026 (3) Å ], with a dihedral angle of 78.18 (12) between the benzene rings of the chromanone and chromenone moieties. In the crystal, there are weak -stacking interactions [minimum ring centroid separation = 3.9286 (17) Å ]. Related literature

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“…For backgound to bis-chromonones, see: Santhosh & Balasubramanian (1991); Panja et al (2009). For related structures, see: Ambartsumyan et al (2012); Nyburg et al (1986); Li et al (2010). Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Jmol (Hanson, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).…”

Section: Related Literaturementioning

confidence: 99%