摘要:
A new one-pot and divergent synthesis of multisubstituted furo[3,2-clquinolines and quinazolin-4(3H)-ones via sequential isocyanide-based three-component/Staudinger/aza-Wittig reactions was developed. The three-component reactions of dialkyl acetylenedicarboxylates, 2-azidobenzaldehydes (or 2-azidobenzoic acids) and isocyanides gave the azide intermediates, which were subsequently treated with triphenylphosphine to produce polysubstituted furo[3,2-clquinolines 6 or quinazolin-4(3H)-ones 10 in good overall yields by tandem Staudinger/aza-Wittig reactions. (C) 2020 Elsevier Ltd. All rights reserved.
作者机构:
[Yu, Yan-Ling; Sun, Mei; Ding, Ming-Wu; Zhao, Long] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ, Wuhan 430079, Peoples R China.
通讯机构:
[Ding, Ming-Wu] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ, Wuhan 430079, Peoples R China.
关键词:
oxidative Ugi reaction;aza-Wittig reaction;1,3,4-oxadiazole;1,2,3,4-tetrahydroisoquinoline;(N-isocyanimine)triphenylphosphorane
摘要:
A one-pot protocol for the synthesis of 5-(1,2,3,4-tetrahydroisoquinolin-1-yl)-1,3,4-oxadiazoles via DEAD-mediated oxidative Ugi/aza-Wittig reaction has been developed. The reaction of (N-isocyanimine)triphenylphosphorane, carboxylic acids, and N-aryl-1,2,3,4-tetrahydroisoquinolines produced polysubstituted 5-(1,2,3,4-tetrahydroisoquinolin-1-yl)-1,3,4-oxadiazoles directly in good yields in the presence of DEAD as an oxidant.
摘要:
A new one-pot four-component preparation of polysubstituted thiazoles by a cascade Ugi/Wittig cyclization has been developed. The four-component reactions of the odorless isocyano(triphenylphosphoranylidene)acetates 1, aldehydes 2, amines 3 and thiocarboxylic acids 4 produced 2,4,5-trisubstituted thiazoles 5 in moderate to good yields in the presence of triethylamine. The two-component reactions between isocyano(triphenylphosphoranylidene)acetates 1 and thiocarboxylic acids 4 in the presence of triethylamine provided the corresponding 4,5-disubstituted thiazoles 6 in good yields as well. (C) 2020 Elsevier Ltd. All rights reserved.
期刊:
The Journal of Organic Chemistry,2019年84(21):14313-14319 ISSN:0022-3263
通讯作者:
Ding, Ming-Wu
作者机构:
[Sun, Mei; Ding, Ming-Wu; Zhao, Long] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Ding, Ming-Wu] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ, Wuhan 430079, Hubei, Peoples R China.
摘要:
A new efficient DEAD-promoted oxidative Ugi/Wittig reaction for the preparation of 2-(1,2,3,4-tetrahydroisoquinolin-1-yl)oxazoles has been developed. The one-pot reactions of odorless isocyano(triphenylphosphoranylidene)acetates, carboxylic acids, and N-aryl-1,2,3,4-tetrahydroisoquinolines produced polysubstituted 2-(1,2,3,4-tetrahydroisoquinolin-1-yl)oxazoles directly in good yields in the presence of DEAD oxidant.
期刊:
The Journal of Organic Chemistry,2019年84(22):14911-14918 ISSN:0022-3263
通讯作者:
He, Ping;Ding, Ming-Wu
作者机构:
[Xiao, Mi-Mi; Cai, Shuang; Yuan, Yue-Fei; He, Ping; Ren, Zhi-Lin] Hubei Univ Arts & Sci, Coll Chem Engn, Xiangyang 441053, Hubei, Peoples R China.;[Lu, Wen-Ting; Ding, Ming-Wu; Ren, Zhi-Lin] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[He, Ping] H;[Ding, Ming-Wu] C;Hubei Univ Arts & Sci, Coll Chem Engn, Xiangyang 441053, Hubei, Peoples R China.;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
摘要:
A one-pot novel strategy is described for the construction of various oxazolo[4,5-c]quinoline derivatives starting from the isocyano(triphenylphosphoranylidene)acetates, aldehydes, amines, and 2-azidobenzoic acids. The reactions generated the target products directly in moderate to good yields via a sequential Ugi/Wittig/aza-Wittig cyclization process. The salient features of the method are that all three groups of the multifunctional isocyanides were involved in the reaction with broad substituent scopes and mild reaction conditions, making the protocol a useful contribution to the synthesis of oxazolo[4,5-c]quinoline heterocycles.
摘要:
An efficient one-pot and regioselective synthesis of 3,4-dihydroquinazolines and 4,5-dihydro-3H-1,4-benzodiazepin-3-ones by Ugi/Staudinger/aza-Wittig sequence has been developed. The Ugi reactions of 2-azidobenzylamines, aldehydes, acids (or alpha-keto acids) and isocyanides produced the azide intermediates, which were then treated with tributylphosphine or triphenylphosphine to give poly-substituted 3,4-dihydroquinazolines or 4,5-dihydro-3H-1,4-benzodiazepin-3-ones in moderate to good yields by tandem Standinger/aza-Wittig reactions. (C) 2019 Elsevier Ltd. All rights reserved.
摘要:
A new efficient and diastereoselective synthesis of multisubstituted isoindolines with two stereogenic centers via sequential Ugi/aza-Michael addition reaction was developed. Ugi-3CR of aldehydes 1, amines 2 and isocyanates 3 in the presence of catalytic amount of H3PO4 produced intermediates 4, which were then transformed to isoindolines 5 with good 1,3-trans diastereoselectivity in the presence of K2CO3 by intramolecular aza-Michael addition. Sequential Ugi-azide and aza-Michael addition reaction of aldehydes 1, amines 2 and trimethylsilyl azide 6 also produced 4-tetrazolyl substituted isoindolines 8 with good 1,3-trans diastereoselectivity in the presence of potassium carbonate. (C) 2019 Elsevier Ltd. All rights reserved.
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.
摘要:
A new facile preparation of furan-2(3H)-ones and 2,3,5-trisubstituted furans by a sequential O-acylation/Wittig(/O-acylation) reaction has been developed. The easily accessible 2-(triphenylphosphoranylidene)-succinic acid 1-ester 3 reacted with acid chloride produced furan-2(3H)-ones 4 in good yields in the presence of DMAP via sequential 0-acylation and intramolecular Wittig reaction of acid anhydride. Subsequently, the 2,3,5-trisubstituted furans 5 were prepared from furan-2(3H)-ones 4 and diverse aryl chlorides in presence of triethylamine through further O-acylation. (C) 2019 Elsevier Ltd. All rights reserved.
期刊:
The 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.
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.
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 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:
The 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.