Domino Synthetic Strategy for Tetrahydrothiopyran Derivatives from Benzaldehydes, 2-Acetylfuran/2-Acetylthiophene, and Sodium Sulfide

被引：8

作者：

Chen, Dongdong ^{[1
]}

Du, Weixia ^{[1
]}

Yang, Xufeng ^{[1
]}

Liu, Tao ^{[1
]}

机构：

[1] Lvliang Univ, Dept Chem & Chem Engn, Lishi 033001, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 14期

关键词：

STEREOSELECTIVE-SYNTHESIS; ELEMENTAL SULFUR; ANALOGS; POTENT; REARRANGEMENT; INHIBITORS; CATALYST; BINDING; DESIGN;

D O I：

10.1021/acs.joc.0c01006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel domino reaction from benzaldehydes and 2-acetylfuran/2-acetylthiophene with sodium sulfide was developed to synthesize a series of tetrahydrothiopyran (THTP) derivatives. The reaction proceeded well to construct a tetrahydrothiopyran ring and five new bonds in one step. A mechanism is proposed, involving a stepwise Aldol/double Michael addition/Aldol (AMMA) reaction cascade. In this transformation, sodium sulfide acts as a nucleophile and base. This method is characterized by transition-metal-free, commercially available starting materials and mild reaction conditions.

引用

页码：9088 / 9095

页数：8

共 10 条

[1] Domino synthetic strategy for tetrahydrothiophene derivatives from 2-acetylfuran/2-acetylthiophene, benzaldehydes, and sulfur powder
Chen, Dongdong
Bai, Yannan
Cheng, Qi
Li, Jingwei
Tong, Zongbo
Hou, Jianfeng
Liu, Tao
Guo, Yuqi
Tang, Xiaolin
Yang, Xue
Yang, Xufeng
ARABIAN JOURNAL OF CHEMISTRY, 2022, 15 (09)
[2] ALKYLATION OF 2-ACETYLFURAN AND 2-ACETYLTHIOPHENE UNDER THE PHASE-TRANSFER CATALYSIS
ABELE, EM
GOLDBERG, YS
POPELIS, YY
SHIMANSKAYA, MV
ZHURNAL ORGANICHESKOI KHIMII, 1990, 26 (08): : 1784 - 1790
[3] Enthalpies of combustion and formation of 2-acetylpyrrole, 2-acetylfuran and 2-acetylthiophene
Flores, Henoc
Adriana Camarillo, E.
Mentado, Juan
THERMOCHIMICA ACTA, 2009, 493 (1-2) : 76 - 79
[4] Determination of rotational constants in the presence of methyl internal rotation: 2-acetylfuran and 2-acetylthiophene as examples
Demaison, Jean
Vogt, Natalja
Nguyen, Ha Vinh Lam
CHEMICAL PHYSICS LETTERS, 2022, 794
[5] SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL SCREENING OF MIXED LIGAND COMPLEXES DERIVED FROM OXIMES OF 2-ACETYLFURAN AND 2-ACETYLTHIOPHENE USING TRANSITION METALS
Sharma, Deepankar
Nag, Purnima
HETEROCYCLIC LETTERS, 2021, 11 (02): : 195 - 202
[6] STRUCTURE AND PROPERTIES OF HETEROCYCLIC-COMPOUNDS AND THEIR COMPLEXES .49. QUANTUM-CHEMICAL STUDY OF 2-ACETYLFURAN, 2-ACETYLTHIOPHENE AND THEIR PROTONATED FORMS
DIMUKHAMEDOV, AI
SADIMENKO, AP
SHEINKER, VN
OSIPOV, OA
ZHURNAL OBSHCHEI KHIMII, 1984, 54 (03): : 674 - 679
[7] 1,4-PENTANDIEN-3-ONES .32. REACTION OF 2-ACETYLTHIOPHENE AND 2-ACETYLFURAN WITH MALONONITRILE AND ALDEHYDES, AND SYNTHESIS AND PROPERTIES OF PHENYLENE-BIS((THIENYL/FURYL)NICOTINONITRILE) DERIVATIVES
GREINERBECHERT, L
OTTO, HH
ARCHIV DER PHARMAZIE, 1991, 324 (09) : 563 - 572
[8] Synthetic Studies on 2H-Thiopyran Compounds: A Reinvestigation of the Reaction Between Benzaldehydes and Sodium Sulfide
Banerji, Avijit
Biswas, Pizush Kanti
Bandyopadhyay, Debasish
Gupta, Maya
Prange, Thierry
Neuman, Alain
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (12) : 3199 - 3211
[9] Domino reactions of 1-(2-alkoxyaryl)-3-akylprop-2-yn-1-ones with sodium sulfide leading to thiochromen-4-one derivatives
Yang, Xiaobo
Li, Shangfu
Liu, Hongxia
Jiang, Yuyang
Fu, Hua
RSC ADVANCES, 2012, 2 (16): : 6549 - 6554
[10] New domino reaction. One pot synthesis of 4,7-dihydroxythioaurone derivatives from benzaldehydes and 4-acetyl-2-oxo-benz[1,3]oxathiole
Konieczny, MT
Konieczny, W
Wolniewicz, S
Wierzba, K
Suda, Y
Sowinski, P
TETRAHEDRON, 2005, 61 (36) : 8648 - 8655

← 1 →