摘要:
A new efficient synthesis of pyrrolidin-2-ones via sequential Wittig reaction/nucleophilic addition/cyclization was developed. The Wittig reaction of the phosphoranes with isocyanates produced ketenimine intermediates that were then treated with primary amines to give amidines, which were treated with catalytic sodium alkoxide to give 2-imino-5-oxopyrrolidine-3-carboxylates in good yields.
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2018年83(20):12921-12930 ISSN:0022-3263
通讯作者:
Ding, Ming-Wu
作者机构:
[Kong, Han-Han; Pan, Hong-Ling; Ding, Ming-Wu] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Hubei Int Sci & Technol Cooperat Base Pesticide &, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Ding, Ming-Wu] C;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Hubei Int Sci & Technol Cooperat Base Pesticide &, Wuhan 430079, Hubei, Peoples R China.
摘要:
A new efficient Ag-catalyed cascade cycloisomerization/aerobic oxidation reaction of a Ugi-azide adduct for the preparation of 3-acylpyrroles using molecular oxygen as the terminal oxidant has been developed. A series of 2-tetrazolyl-substituted 3-acylpyrroles were obtained in 62–89% yields from readily available enynals 1, primary amines 2, isocyanides 3, and trimethylsilyl azide 4 in the presence of a catalytic amount of AgNO3 and DMAP under an O2 atmosphere.
摘要:
A new and efficient synthesis of 1,2,4-trisubstituted furans from a Baylis–Hillman β-bromo aldehyde, an acid, an isocyanide, and methyl(diphenyl)phosphine, by a sequential Passerini condensation, Wittig reaction, and isomerization in the presence of triethylamine is reported.
作者机构:
[Lu, Wen-Ting; Sun, Mei; Ding, Ming-Wu; He, Ping; Ren, Zhi-Lin] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Ding, Ming-Wu] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Wuhan 430079, Hubei, Peoples R China.
摘要:
A robust ligand-free palladium-catalyzed cascade reaction for the synthesis of diversely substituted iminoisoindolinones has been developed. The cascade reaction involves isocyanide insertion into Ugi-3CR adducts, accompanied by unexpected hydroxylation and rearrangement.
摘要:
A facile, one-pot synthesis of multisubstituted quinoxalin-2(1H)-ones via a Ugi 4CR/catalytic aza-Wittig sequence has been developed. In the presence of a catalytic amount of 3-methyl-1-phenyl-2-phospholene 1-oxide, the reaction of 2-aminobenzoyl azides, aldehydes, ketoacids, and isocyanides selectively produces quinoxalin-2(1H)-ones as the sole products in high yields.
摘要:
A new efficient synthesis of multisubstituted 1H-imidazo-[4,5-c]quinoline derivatives via sequential van Leusen/Staudinger/aza-Wittig/carbodiimide-mediated cyclization was developed. Azides 4, obtained from Van Leusen reaction of 2-azidobenzaldehyde 1, amine 2 and TosMIC (tosylmethyl isocyanide) 3, reacted with triphenyl phosphine to produce iminophosphorane 5. A tandem aza-Wittig reaction of iminophosphorane 5 with isocyanate generated 1H-imidazo-[4,5-c]quinoline 7 through carbodiimide intermediate 6 in moderate to good yield. (C) 2018 Elsevier Ltd. All rights reserved.
摘要:
An efficient one-pot synthesis of quinazolin-4(3H)-ones, benzoimidazo[2,1-b]quinazolin-12(6H)-ones and imidazo[2,1-b]quinazolin-5(1H)-ones via a palladium-catalyzed domino process has been developed. The Pd-catalyzed reactions of 2-azidobenzamides 1 with isocyanides 2 produced quinazolin-4(3H)ones 4 at room temperature by a domino Pd-catalyzed cross-coupling/carbodiimide-mediated cyclization. However, as 2-azido-N-(2-bromophenyl)benzamides 1 were used under heating condition in the presence of Cs2CO3, the benzoimidazo[2,1-b]quinazolin-12(6H)-ones 5 were directly obtained by twice Pd-catalyzed domino cyclization. A domino reogioselective 5-exo-dig intramolecular cyclization reaction of alkynyl-containing azides 6 with isocyanides 2 generated imidazo[2,1-b]quinazolin-5(1H)-ones 9 in 74 -93% yields in the presence of catalyst Pd(PPh3)(4) and K2CO3. (C) 2017 Elsevier Ltd. All rights reserved.
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2017年82(5):2772-2776 ISSN:0022-3263
通讯作者:
Ding, Ming-Wu
作者机构:
[Rao, Yong; Yan, Yan-Mei; Ding, Ming-Wu] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构:
[Ding, Ming-Wu] C;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
A new one-pot preparation of indoles by a Ugi-3CR/Wittig sequence has been developed. The reaction of odorless isocyanide-substituted phosphonium salt 5, aldehyde 6, and amine 7 produced the indoles 9 in 45–82% yields via a sequential Ugi-3CR/Wittig reaction in the presence of H3PO4 and solid K2CO3, respectively.
摘要:
Iminophosphoranes reacted with CS2 at –5 °C to produce the isothiocyanates, which were treated with primary amine to give thioureas in 73–91% yields. The subsequent reaction of thioureas with alkyl bromides in the presence of solid K2CO3 produced 2-alkylthiopyrimidin-4(3H)-ones in 68–88% yield via tandem intramolecular cyclization–isomerization–S-alkylation.
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2017年82(24):13735-13739 ISSN:0022-3263
通讯作者:
Ding, Ming-Wu
作者机构:
[Wei, Xiao; Xiong, Jun; Liu, Zi-Ming; Ding, Ming-Wu] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Ding, Ming-Wu] C;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
摘要:
A new one-pot preparation of polysubstituted imidazoles by a Staudinger/aza-Wittig/Ag(I)-catalyzed cyclization/isomerization has been developed. The easily accessible propargylazide derivatives reacted with triphenylphosphine, isocyanates, and amines sequentially to produce the fully substituted imidazoles in good overall yields in the presence of catalytic amount of AgNO3/DMAP.
摘要:
A new one-pot and regioselective synthesis of 3,4-dihydroquinazolines by Ugi/Staudinger/aza-Wittig sequence has been developed. The Ugi-type reaction of 2-azidobenzylisocyanide, aldehyde, secondary amine and acid produced an azide intermediate, which was then treated with triphenylphosphine to give 3,4-dihydroquinazolines regioselectively in good overall yields by Staudinger/aza-Wittig reaction at room temperature.
期刊:
European Journal of Organic Chemistry,2017年2017(18):2560-2560 ISSN:1434-193X
通讯作者:
Ming-Wu Ding
作者机构:
[Mei Sun; Ming-Wu Ding] Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, 430079 Wuhan, Hubei, China;College of Materials and Chemical Engineering, China Three Gorges University, 443002 Yichang, Hubei, China;[Long Wang] Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, 430079 Wuhan, Hubei, China<&wdkj&>College of Materials and Chemical Engineering, China Three Gorges University, 443002 Yichang, Hubei, China
通讯机构:
[Ming-Wu Ding] K;Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, 430079 Wuhan, Hubei, China