Synthesis of new alkoxy/alkylthiovinylated oxazoles using tosylmethyl isocyanide

Вчисло, Надежда В.; Fedoseeva, Victoria G.; Новокшонов, В. В.; Ларина, Л. И.; Розенцвейг, И. Б.; Verochkina, Ekaterina A.

doi:10.1016/j.mencom.2020.05.030

Cited by 7 publications

(4 citation statements)

References 32 publications

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“…Synthesis of oxazole 2 was carried out according to the published procedure. 24 To a solution of aldehydes 1 (1 mmol) in a 6 ml of MeOH, was added TosMIC (1.1 mmol) and K2CO3 (1.4 mmol). The reaction mixture was stirred for 3 h at 55-60 °C.…”

Section: Methodsmentioning

confidence: 99%

“…NMR 1 H (CDCl3): δ = 0.84 (t, 3H, J 7.2 Hz, CH3 (SBu)), 0.90 (t, 3H, J 7.3 Hz, CH3 (SBu)), 1.25-1.59 (m, 8H, SCH2CH2CH2 (2SBu)), 2.12-2.42 (m, 4H, CH2 at C-3' and C-4'), 2.50-2.60 (m, 4H, 2SCH2), 6.64 (s, 1H, H-4), 7.08 (s, 1H, =CH), 7.85 (s, H-2). NMR 13 (10), 168 (19), 152 (7), 127 (100), 123 (6), 99 (8), 85 (23), 83 (27), 57 (21), 43 (24)…”

Section: Methodsmentioning

confidence: 99%

“…The reaction mixture was refluxed for 2-6 h. The solvent was removed under vacuum, and the residue was purified by column chromatography (SiO2, eluentchloroform). (6), 298 [M] + -SBu (6), 271 (7), 253 (37), 238 (9), 184 (7), 168 (5), 158 (53), 144 (6), 126 (26), 115 (9), 99 (14), 85 (20), 81 (24) (24), 356 (3), 312 (18), 267 (92), 238 (13), 228 (7), 211 (10), 200 (11), 184 (21), 172 (92), 155 (8), 144 (17), 126 (33), 112 (11), 99 (21), 85 (23), 71 (23), 57 (60), 55 (33), 41 (100). Calculated C19H31S2O4N (%): C, 56.86; H, 7.73; S, 15.96; N, 3.49.…”

Section: Synthesis Of Oxazolines (3)mentioning

confidence: 99%

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2,5-Bis-(butylsulfanyl)-2,3-dihydro-4H-pyran-2-carbaldehyde in the synthesis of five-membered heterocycles

Vchislo¹,

Verochkina²,

Fedoseeva³

et al. 2023

Arkivoc

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Five-membered, nitrogen-containing heterocycles such as oxazole, oxazoline and imidazolidine are important structural motifs of many natural and synthetic compounds, as well as drugs with diverse bioactivity. An efficient strategy for the synthesis of new heterocyclic compounds such as 1,3-oxazole, 1,3-oxazoline and 1,3imidazolidine from 2,5-bis-(butylsulfanyl)-2,3-dihydro-4H-pyran-2-carbaldehyde has been developed.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Synthesis Of Oxazolines (3)mentioning

confidence: 99%

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2,5-Bis-(butylsulfanyl)-2,3-dihydro-4H-pyran-2-carbaldehyde in the synthesis of five-membered heterocycles

Vchislo¹,

Verochkina²,

Fedoseeva³

et al. 2023

Arkivoc

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“…Unlike classical protocols using alkali [ 42 , 43 , 44 ], heterogenous system solid NaOH/DMF(MeCN) allows the avoidance of by-products and increase in yields of the target compounds. α-Alkoxy- and α-alkylthiosubstituted α,β-unsaturated aldehydes 29 are valuable building blocks in the synthesis of oxazoles, pyrroles, and quinoxalines [ 45 ].…”

Section: Synthesis Of α-Functionally Substituted αβ-Unsaturated Aldehydesmentioning

confidence: 99%

α-Functionally Substituted α,β-Unsaturated Aldehydes as Fine Chemicals Reagents: Synthesis and Application

2021

Self Cite

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α-Functionalized α,β-unsaturated aldehydes is an important class of compounds, which are widely used in fine organic synthesis, biology, medicine and pharmacology, chemical industry, and agriculture. Some of the 2-substituted 2-alkenals are found to be the key metabolites in plant and animal cells. Therefore, the development of efficient methods for their synthesis attracts the attention of organic chemists. This review focusses on the recent advances in the synthesis of 2-functionally substituted 2-alkenals. The approaches to the preparation of α-alkyl α,β-unsaturated aldehydes are not included in this review.

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Hydroformylation of Alkynyl Sulfides: A Stereo‐ and Regioselective Route to α‐Sulfenyl Acroleins

Wagner,

Gulea,

Girard

2024

Adv Synth Catal

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The rhodium‐catalyzed hydroformylation of alkynyl sulfides under mild conditions is described. The method gives access to α‐sulfenyl acroleins with good regioselectivities (ratio α/β up to 89/11) and is applicable to variously substituted substrates. It is effective even on more complex substrates, such as cysteine and cholesterol derivatives. To demonstrate the synthetic potential of the obtained products, (Z)‐3‐cyclohexyl‐2‐methylsulfenyl acrolein was selected as an example and its sulfur atom selectively oxidized to the corresponding sulfoxide or sulfone. Acid‐promoted (Z) to (E) isomerization of the double bond occurred during oxidation. The three obtained sulfenyl‐, sulfinyl‐, and sulfonyl‐functionalized acroleins have been then used as dienophiles to access cyclohexene carbaldehydes.

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Synthesis of new alkoxy/alkylthiovinylated oxazoles using tosylmethyl isocyanide

Cited by 7 publications

References 32 publications

2,5-Bis-(butylsulfanyl)-2,3-dihydro-4H-pyran-2-carbaldehyde in the synthesis of five-membered heterocycles

2,5-Bis-(butylsulfanyl)-2,3-dihydro-4H-pyran-2-carbaldehyde in the synthesis of five-membered heterocycles

α-Functionally Substituted α,β-Unsaturated Aldehydes as Fine Chemicals Reagents: Synthesis and Application

Hydroformylation of Alkynyl Sulfides: A Stereo‐ and Regioselective Route to α‐Sulfenyl Acroleins

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