作者机构:
[Guan, Zhi-Rong; Kong, Han-Han; Ding, Ming-Wu; Ren, Zhi-Lin] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, 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, Minist Educ, Wuhan 430079, Hubei, Peoples R China.
摘要:
The multifunctional odorless isocyano(triphenylphosphorany-lidene)acetate was prepared as a new stable phosphorus ylide containing isocyanide group. A new one-pot four component synthesis of multisubstituted oxazoles by a cascade Ugi/Wittig process without Mumm rearrangement has been developed, starting from the isocyano(triphenylphosphora-nylidene)acetates, aldehydes, amines and acids. Two component reactions of isocyano(triphenylphosphoranylidene)-acetates and acids also generated disubstituted oxazoles in good yields.
作者机构:
[Yan, Yan-Mei; Ding, Ming-Wu; Gao, Yun] 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.
关键词:
Ugi reaction;aza-Wittig reaction;C-H activation;Benzimidazole Quinoxalin-2(1H)-one
摘要:
An efficient preparation of multisubstituted benzimidazoles and quinoxalin-2(1H)-ones by Ugi 4CC/aza-Wittig sequence was developed. The 2-azidobenzenamines, obtained from C-H activation of aromatic amine precursors, reacted with aldehydes, acids, and isocyanides to produce Ugi products, which were transformed to the benzimidazoles or quinoxalin-2(1H)-ones in moderate to good yields in further reaction with triphenylphosphine. (C) 2016 Elsevier Ltd. All rights reserved.
作者机构:
[Wang, Long; Guan, Zhi-Rong; Ding, Ming-Wu] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Wang, Long] China Three Gorges Univ, Coll Mat & Chem Engn, Yichang 443002, 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, Peoples R China.
摘要:
A one-pot synthesis of 1H-isochromenes and 1,2-dihydroisoquinolines by a I-MCR/Wittig sequence was developed. The reaction of phosphonium salt 5, an acid, an amine ( or without), and an isocyanide gave the 1H-isochromenes 7 or 1,2-dihydroisoquinolines 9 in good yields by a sequential Passerini or Ugi condensation and an intramolecular Wittig reaction in the presence of K2CO3.
摘要:
A new efficient synthesis of isoquinoline-1,3(2H,4H)-diones or isoindolin-1-ones via sequential Ugi-4CR or Ugi-3CR/cyclization reaction was developed. α-Acylamino amides 5, obtained from Ugi-4CR of methyl 2-formylbenzoate, amines, isocyanates and acids, cyclized to give isoquinoline-1,3(2H,4H)-diones 6 in good yields in the presence of catalytic amount of sodium ethoxide. Ugi-3CR of methyl 2-formylbenzoate, amines and isocyanates in the presence of catalytic amount of H3PO4 produced isoindolin-1-ones 7 directly in one-pot fashion.
摘要:
N-[2-(Alkylamino)-1-(2-azidophenyl)-2-oxoethyl]-N-(3-oxoprop-1-en-2-yl)amides, obtained from the Ugi reaction of a vinyliminophosphorane, 2-azidobenzaldehyde, a carboxylic acid, and an alkyl isocyanide, reacted with triphenylphosphine to give various 3-arylidene-3H-1,4-benzodiazepine in good yields via sequential Staudinger and intramolecular aza-Wittig reaction.
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2016年81(3):1263-1268 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, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
通讯机构:
[Ding, Ming-Wu] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
摘要:
A simple and one-pot synthesis of multisubstituted benzimidazoles by a Ugi 4CC/catalytic aza-Wittig sequence was developed. The reaction of 2-aminobenzoyl azide 2, aldehyde 3, acid 4, and isocyanide 5 produced the benzimidazoles 8 in moderate to good yields via a sequential Ugi condensation and catalytic aza-Wittig in the presence of a catalytic amount of phospholene oxide.
摘要:
Iminophosphoranes 3, obtained from the Baylis–Hillman adducts, reacted with 2-azidobenzoyl chloride to give the azides 4. The sequential reaction of azides 4 with triphenylphosphine and isocyanate produced 1H-pyrimido[2,1-b]quinazoline-2,6-diones 9 in the presence of sodium ethoxide via a tandem aza-Wittig/nucleophilic addition/intramolecular cyclization/isomerization reaction.
摘要:
A one-pot synthetic approach to isoquinolin-1(2H)-ones through a Ugi/Wittig sequence has been developed. The reaction of phosphonium salt, aldehyde, secondary amine, and isocyanide produced isoquinolin-1(2H)-ones in good yields through sequential Ugi condensation and intramolecular Wittig reaction in the presence of K<sub>2</sub>CO<sub>3</sub>.
作者机构:
[Zeng, Xiao-Hua; Wang, Hong-Mei; Ding, Ming-Wu] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Zeng, Xiao-Hua; Wang, Hong-Mei] Hubei Univ Med, Renmin Hosp, Lab Chinese Herbal Pharmacol, Shiyan 442000, 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 one-pot synthetic approach to 5,6-dihydropyridin-2(1H)-ones has been developed using a domino process involving Ugi, aldol, and hydrolysis reactions, starting with Baylis–Hillman phosphonium salts, primary amines, isocyanides, and arylglyoxals.
期刊:
Journal of Heterocyclic Chemistry,2014年51(S1):E93-E97 ISSN:0022-152X
通讯作者:
Ding, Ming-Wu
作者机构:
[Yan, Yan-Mei; Ding, Ming-Wu; He, Ping] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;[He, Ping] Hubei Univ Arts & Sci, Coll Chem Engn & Food Sci, Xiangyang 441053, Peoples R China.
通讯机构:
[Ding, Ming-Wu] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
摘要:
The iminophosphorane (3), obtained from reaction of ethyl 3-amino-4-cyano-1-phenyl-1H-pyrrole-2-carboxylate (2) with triphenylphosphine, hexachloroethane, and triethylamine, reacted with aromatic isocyanates to give carbodiimides (4). Further reaction of 4 with various amines, phenols, or ROH to give 2,3,5,7-tetrasubstituted 3H-pyrrolo[3,2-d]pyrimidine-4(5H)-ones (6) in satisfactory yields in the presence of catalytic amount of sodium alkoxide or solid potassium carbonate.
摘要:
Vinyl azides, obtained from the Ugi-type reaction of 2-azido-3-arylacrylic acid, secondary amine, aldehyde, and isocyanide, react with triphenylphosphine to give a variety of 4-arylidene-1H-imidazol-5(4H)-ones in high yields via sequential Staudinger and intramolecular aza-Wittig reaction.