Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid

被引：1

作者：

Mammeri, Oussama Abdelhamid ^{[1
]}

Baranov, Ilia M. ^{[1
]}

Ivanov, Alexandr Yu ^{[2
]}

Boyarskaya, Irina A. ^{[1
]}

Vasilyev, Aleksander. V. ^{[1
,3
]}

机构：

[1] St Petersburg State Univ, Inst Chem, 7-9 Univ Nab, St Petersburg 199034, Russia

[2] St Petersburg State Univ, Ctr Magnet Resonance, Res Pk, Univ Pr 26, St Petersburg 198504, Petrodvoretz, Russia

[3] St Petersburg State Forest Tech Univ, Dept Chem, Inst Per 5, St Petersburg 194021, Russia

来源：

TETRAHEDRON | 2023年 / 146卷

关键词：

Allene carboxylates; Furanones; Triflic acid; Carbocations; Electrophilic activation; ESTERS; 2,3-ALLENOATES; BUTENOLIDES; INVOLVEMENT; IODINATION; GENERATION; CHEMISTRY; DIENES; ACCESS; IONS;

D O I：

10.1016/j.tet.2023.133649

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkyl allene carboxylates [R2(R3)C=C=C(R1)-C(=O)OAlk] in Bronsted superacid CF3SO3H (triflic acid, TfOH) at room temperature or 70 degrees C for 30 min are cyclized to form 2-(5H)-furanones in yields up to 83%. The reaction cationic intermediates, O-monoprotonated [R2(R3)C=C=C(R1)-C(=O+H)OAlk] and O,C-diprotonated [R2(R3) C+-CH=C(R1)-C(=O+H)OAlk] forms of starting allenes, have been studied experimentally by NMR and theoretically by DFT calculations. It has been found that the cyclization proceeds via O,C-diprotonated forms of starting allenes.

引用

页数：8

共 50 条

[1] SYNTHESIS OF 4-ALKYL-2(5H)-FURANONES
KAMETANI, T
KATOH, T
TSUBUKI, M
HONDA, T
CHEMICAL & PHARMACEUTICAL BULLETIN, 1985, 33 (01) : 61 - 66
[2] SYNTHESIS OF 5-ALKYL-4-BROMO-5-HYDROXY-2(5H)-FURANONES AND 5-ALKYLIDENE-4-BROMO-2(5H)-FURANONES
FONT, J
GRACIA, A
DEMARCH, P
TETRAHEDRON LETTERS, 1990, 31 (38) : 5517 - 5520
[3] An efficient synthesis of brominated 4-alkyl-2(5H)-furanones
Iskander, George
Zhang, Ruonan
Chan, Daniel Shiu-Hin
Black, David Stc
Alamgir, Mahiuddin
Kumar, Naresh
TETRAHEDRON LETTERS, 2009, 50 (32) : 4613 - 4615
[4] NEW METHODS FOR THE SYNTHESIS OF 3(2H)-FURANONES AND 2(5H)-FURANONES
SAIMOTO, H
SHINODA, M
MATSUBARA, S
OSHIMA, K
HIYAMA, T
NOZAKI, H
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (10) : 3088 - 3092
[5] New advances in the synthesis of 2(5H)-furanones
Li, Bing-Zhou
Chen, Wei-Min
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (01) : 29 - 36
[6] NEW METHODS FOR THE SYNTHESIS OF 3(2H)-FURANONES AND 2(5H)-FURANONES
SAIMOTO, H
MATSUBARA, S
OSHIMA, K
HIYAMA, T
NOZAKI, H
HETEROCYCLES, 1984, 21 : 600 - 600
[7] The chemistry of 2(5H)-furanones
Hashem, A
Kleinpeter, E
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 81, 2001, 81 : 107 - 165
[8] ON THE SYNTHESIS OF 4-ALKOXY-2(5H)-FURANONES
ZIMMER, H
AMER, A
VANPHAM, C
SCHMIDT, DG
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14): : 3368 - 3370
[9] PHOTOCHEMISTRY OF 2(3H)-FURANONES AND 2(5H)-FURANONES
FILLOL, L
MIRANDA, MA
MORERA, IM
SHEIKH, H
HETEROCYCLES, 1990, 31 (04) : 751 - 782
[10] BUTENOL SYNTHESES .3. CONVENIENT SYNTHESIS OF 5-ALKYLIDENE-2(5H)-FURANONES, 2(5H)-FURANONES AND 2-ETHOXYFURANS
SAALFRANK, RW
HAFNER, W
MARKMANN, J
BESTMANN, HJ
TETRAHEDRON, 1988, 44 (16) : 5095 - 5100

← 1 2 3 4 5 →