摘要：
A novel and efficient Ugi four-component domino dicyclization strategy has been developed for one-step constructing diverse 3-(1,3,4-oxadiazol-2-yl)isoindolin-1-ones with good yields, without the need for additional additives. This domino dicyclization process underwent three consecutive reactions including Ugi, aza-Wittig and N-acylation by utilizing (N-isocyanimine)triphenylphosphorane, methyl 2-formylbenzoate, primary amines, and carboxylic acids. The initial biological activity testing revealed that compound 5 i exhibited good antifungal activity against certain fungi and demonstrated versatile applications in the fields of pesticide chemistry. We developed an efficient one-step method for the preparation of polysubstituted 3-(1,3,4-Oxadiazol-2-yl)isoindolin-1-ones via Ugi four-component domino dicyclization starting from the easily accessible (N-isocyanimine)triphenylphosphorane under mild reaction conditions. image
摘要：
A novel metal-free synthesis of 3-substituted isocoumarins through a sequential O-acylation/Wittig reaction has been established. The readily accessible (2-carboxybenzyl)-triphenylphosphonium bromide and diverse chlorides produced various 1H-isochromen-1-one in the presence of triethylamine, employing sequential O-acylation and an intramolecular Wittig reaction of acid anhydride. Reactions using these facile conditions have exhibited high functional group tolerance and excellent yields (up to 90%). Moreover, the fluorescence properties of isocoumarin derivatives were evaluated at the theoretical and experimental levels to determine their potential application in fluorescent materials. These derivatives have good photoluminescence in THF with a large Stokes shift and an absolute fluorescence quantum yield of up to 14%.
期刊：
JOURNAL OF ORGANIC CHEMISTRY,2023年88(3):1898-1906 ISSN：0022-3263
作者机构：
[Yang, Mao-Lin; Chen, Hao-Ran; 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.
摘要：
A new efficient and stereoselective synthesis of 12-tetrazolyl substituted (E)-5H-quinazolino[3,2-a]quinazolines via sequential Ugi-azide/Staudinger/aza-Wittig/addition/Ag(I)-catalyzed cyclization was developed. The four-component reactions of 2-azidobenzaldehyde, 2-(alkynyl)benzenamine, isocyanide, and trimethylsilyl azide gave Ugi-azide intermediates, which were subsequently treated with triphenylphosphine and isocyanate to produce 12-tetrazolyl substituted (E)-5H-quinazolino[3,2-a]quinazolines in the presence of Ag(I) catalyst and K(2)CO(3).
摘要：
<jats:p>A new efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4<jats:italic>H</jats:italic>-3,1-benzothiazines via sequential Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reaction has been developed. The three-component Passerini reactions of 2-azidobenzaldehydes <jats:bold>1</jats:bold>, benzoic acid (<jats:bold>2</jats:bold>), and isocyanides <jats:bold>3</jats:bold> produced the azide intermediates <jats:bold>4</jats:bold>, which were treated sequentially with triphenylphosphine, isocyanates (or CS<jats:sub>2</jats:sub>), and secondary amines to give polysubstituted 3,4-dihydroquinazolines <jats:bold>8</jats:bold> and 4<jats:italic>H</jats:italic>-3,1-benzothiazines <jats:bold>11</jats:bold> in good overall yields through consecutive Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reactions.</jats:p>
作者机构：
[Ding Mingwu; Zhao Long; Chen Haoran; Yang Maolin] Cent China Normal Univ, Key Lab Pesticide & Chem Biol Minist Educ, Wuhan 430079, Peoples R China.
关键词：
3,4-dihydroquinazoline-one;iminophosphorane;isocyanide;oxidative Ugi reaction;aza-Wittig reaction
摘要：
A new one-pot synthesis of 3,4-dihydroquinazolines by diethyl azodicarboxylate (DEAD)-promoted oxidative Ugi/ aza-Wittig reaction was developed. The reactions of iminophosphoranes 5, N-aryl-1,2,3,4-tetrahydroisoquinolines 6 and acids 7 produced 3-(tetrahydroisoquinolin-1-formyl) substituted 3,4-dihydroquinazolines 8 in moderate to good yields in the presence of DEAD by tandem oxidative Ugi/aza-Wittig reaction.
作者机构：
[Yang, Mao-Lin; Sun, Mei; Ding, Ming-Wu; Zhao, Long] Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构：
[Ding, Ming-Wu] C;Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
关键词：
isoquinolin-1(2H )-one;oxidative Ugi reaction;Wittig reaction;(2-carboxybenzyl)triphenylphosphonium salt;1,2,3,4-tetrahydroisoquinoline
摘要：
<jats:title>Abstract</jats:title><jats:p>A new one-pot synthesis of 3-(1,2,3,4-tetrahydroisoquinolin-1-yl)-isoquinolin-1(2H)-ones by DEAD-promoted oxidative Ugi–Wittig reaction was developed. The sequential reactions of (2-carboxybenzyl)triphenylphosphonium salts, isocyanides, and N-aryl-1,2,3,4-tetrahydroisoquinolines produced 3-(1,2,3,4-tetrahydroisoquinolin-1-yl)-isoquinolin-1(2H)-ones in moderate to good overall yields in the presence of DEAD and Et3N.</jats:p>
作者机构：
[Kong, Han-Han; Yang, Mao-Lin; Pan, Hong-Ling; Ding, Ming-Wu] Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构：
[Ming-Wu Ding] K;Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan 430079, P. R. China
作者机构：
[阳茂林; 赵龙; 陈皓冉; 丁明武] Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan, 430079, China
通讯机构：
[Ding, M.] K;Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, China
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：
[Mu, Zhi-Ying; Yao, Gang; Pang, Yong-Long; Xiong, Jun; Zhang, Jia-An; Shi, Hang; He, Hui-Ting; Feng, Qi-Xun] Hubei Univ Sci & Technol, Sch Pharm, Xianning 437100, Hubei, Peoples R China.;[Ding, Ming-Wu] Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
通讯机构：
[Jun Xiong] S;[Ming-Wu Ding] K;Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan, Hubei, 430079 China<&wdkj&>School of Pharmacy, Hubei University of Science and Technology, Xianning, Hubei, 437100 China
摘要：
A simple one pot synthesis of polysubstituted pyrroles via ketenimine formation/Ag(I)-catalyzed alkyne cycloisomerisation has been developed. The easily accessible phosphorane ylide derivatives reacted with isocyanates, producing highly active ketenimines that were then treated with amines, which afforded substituted pyrroles by a 5-exo-dig cyclization/isomerization in the presence of a Ag(I) catalyst in good overall yields.
期刊：
Journal of Chemical Research,2021年45(5-6):395-399 ISSN：1747-5198
通讯作者：
Xiao-Hua Zeng
作者机构：
[Wang, Hong-Mei; Zhu, Xiu-Lian] Hubei Univ Med, Dongfeng Hosp, Expt Ctr Med, Shiyan, Peoples R China.;[Wang, Hong-Mei; Zhu, Xiu-Lian; Chen, Qin-Hua] Shenzhen Baoan Authent TCM Therapy Hosp, Shenzhen 518101, Guangdong, Peoples R China.;[Zeng, Xiao-Hua; Wang, Hong-Mei; Zhu, Xiu-Lian] Hubei Univ Med, Sch Pharmaceut Sci, Hubei Key Lab Wudang Local Chinese Med Res, Shiyan 442000, Peoples R China.;[Ding, Ming-Wu] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构：
[Xiao-Hua Zeng] H;Hubei Key Laboratory of Wudang Local Chinese Medicine Research, School of Pharmaceutical Sciences, Hubei University of Medicine, Shiyan, P.R. China
摘要：
<jats:p> An efficient one-pot base-mediated approach to ( E)-2-aroyl-4-arylidene-5-oxotetrahydro-furans is developed. Nine ( E)-2-aroyl-4-arylidene-5-oxotetrahydrofurans are synthesized in good yields via tandem Passerini and cyclization reactions, starting from Baylis–Hillman acids, aryl glyoxals, and isocyanides at room temperature in the presence of Cs<jats:sub>2</jats:sub>CO<jats:sub>3</jats:sub>. In addition, the MTT assay is used to evaluate their cytotoxicities toward the cervical cancer cell lines C-33A, CaSki, and SiHa and the hepatocarcinoma cell line HepG2. The results show that some of the compounds inhibit the proliferation of cancer cells significantly. </jats:p>
作者机构：
[Yu, Yan-Ling; Sun, Mei; Ding, Ming-Wu; Zhao, Long] Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Sun, Mei] Huainan Normal Univ, Sch Chem & Mat Engn, Huainan 232038, Peoples R China.
通讯机构：
[Ming-Wu Ding] K;Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan, 430079, PR China
关键词：
Quinazolin-4(3H)-one;Oxidative Ugi reaction;Aza-Wittig reaction;Copper catalyzed reaction;Tertiary amine
摘要：
A new one-pot preparation of polysubstituted quinazolin-4(3H)-ones by a sequential oxidative Ugi/ Staudinger/aza-Wittig reaction has been developed. The CuCl/TBHP/DMBP-mediated oxidative Ugi re-actions of tertiary amines 1, 2-azidobenzoic acids 2 and isocyanides 3 produced the azide intermediates, which were directly treated with triphenylphosphine to produce polysubstituted quinazolin-4(3H)-ones 6 in moderate to good yields. (c) 2021 Elsevier Ltd. All rights reserved.
期刊：
JOURNAL OF ORGANIC CHEMISTRY,2021年86(15):10755-10761 ISSN：0022-3263
通讯作者：
Ming-Wu Ding
作者机构：
[Wu, Jing; Yang, Mao-Lin; Ding, Ming-Wu; Zhao, Long] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Hubei Int Sci & Technol Cooperat Base Pesticide &, Wuhan 430079, Peoples R China.
通讯机构：
[Ming-Wu Ding] K;Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan 430079, P. R. China
摘要：
A new efficient synthesis of polysubstituted pyrazin-2(1H)-ones via the sequential Ugi/Staudinger/aza-Wittig/isomerization reaction has been developed. The four-component Ugi reactions of arylglyoxals 1, primary amines 2, α-azidovinyl acids 3, and isocyanides 4 produced the azides 5, which were treated with triphenylphosphine to give pyrazin-2(1H)-ones 6 in good yields through domino Staudinger/aza-Wittig/isomerization reactions.
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.
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：
<jats:title>Abstract</jats:title><jats:p>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.</jats:p>
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.
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.
