Ming-Wu Ding

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Name: 丁明武; MingWu Ding

Organization: Central China Normal University , China

Department: Central China Normal University

Title: Professor(PhD)

TOPICS

Applied Chemistry

Organic Chemistry

Chemicals
References

One-Pot Synthesis of Indoles by a Sequential Ugi-3CR/Wittig Reaction Starting from Odorless Isocyanide-Substituted Phosphonium Salts

Co-reporter:Yan-Mei Yan;Yong Rao

The Journal of Organic Chemistry March 3, 2017 Volume 82(Issue 5) pp:2772-2776

Publication Date(Web):February 6, 2017

DOI:10.1021/acs.joc.7b00004

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.

One-Pot Synthesis of Polysubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Ag(I)-Catalyzed Cyclization/Isomerization

Co-reporter:Jun Xiong, Xiao Wei, Zi-Ming Liu, and Ming-Wu Ding

The Journal of Organic Chemistry December 15, 2017 Volume 82(Issue 24) pp:13735-13735

Publication Date(Web):November 17, 2017

DOI:10.1021/acs.joc.7b02606

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.

Synthesis of fluorescent trisubstituted oxazoles via a facile tandem Staudinger/aza-Wittig/isomerization reaction

Co-reporter:Hai Xie, Yong Rao, Ming-Wu Ding

Dyes and Pigments 2017 Volume 139(Volume 139) pp:

Publication Date(Web):1 April 2017

DOI:10.1016/j.dyepig.2016.12.040

•A new facile synthesis of trisubstituted oxazoles starting from azides was developed.•Some of the oxazole derivatives showed reasonable fluorescence.•The 2,5-diaryl substituted oxazoles gave The greatest fluorescence intensity.A new facile synthesis of trisubstituted oxazoles starting from azides was developed. The reactions of azides with triphenyl phosphine afforded the corresponding 2,4,5-trisubstituted oxazole derivatives via tandem Staudinger, aza-Wittig and isomerization reaction either thermally or under basic conditions. Properties of the oxazole derivatives were surveyed and some of the examples showed reasonable fluorescence. The greatest fluorescence intensity was observed when the 2- and the 5- substituents on the oxazole ring were aromatic groups (with ε = 2.3–3.0 × 104 mol−1 dm3 cm−1 and Φ = 0.25–0.29 relative to quinine sulphate). However, the fluorescence intensity was diminished when either the 2- or the 5-substituent was H or alkyl.Download high-res image (112KB)Download full-size image

Catalytic Intramolecular Wittig Reaction Based on a Phosphine/Phosphine Oxide Catalytic Cycle for the Synthesis of Heterocycles

Co-reporter:Long Wang;Mei Sun

European Journal of Organic Chemistry 2017 Volume 2017(Issue 18) pp:2568-2578

Publication Date(Web):2017/05/10

DOI:10.1002/ejoc.201601628

The catalytic intramolecular Wittig reactions of carbonyl-containing bromides are reported. The R3PO byproducts participate in the catalytic cycle; therefore, the Wittig reaction can be accomplished with only a catalytic amount of organophosphorus reagent. The reaction has also been applied to the efficient and selective synthesis of isoquinolin-1(2H)-ones, indoles, 2,3-dihydro-1H-2-benzazepin-1-ones, benzofurans, and 1,2-dihydroquinolines with a catalytic amount of phosphine oxide (0.1 equiv.) and a tetramethyldisiloxane/titanium isopropoxide [TMDS/Ti(OiPr)4] reductant system (yields: 35–88 %).

Front Cover: Catalytic Intramolecular Wittig Reaction Based on a Phosphine/Phosphine Oxide Catalytic Cycle for the Synthesis of Heterocycles (Eur. J. Org. Chem. 18/2017)

Co-reporter:Long Wang;Mei Sun

European Journal of Organic Chemistry 2017 Volume 2017(Issue 18) pp:2560-2560

Publication Date(Web):2017/05/10

DOI:10.1002/ejoc.201700593

The cover picture shows the catalytic intramolecular Wittig reaction starting from carbonyl-containing bromides. The byproduct R3PO participates in the catalytic cycle; therefore, the Wittig reaction can be accomplished with only a catalytic amount of the organophosphorus reagent. The reaction has also been applied to the efficient and selective synthesis of isoquinolin-1(2H)-ones, indoles, 2,3-dihydro-1H-2-benzazepin-1-ones, benzofurans, and 1,2-dihydroquinolines by using a catalytic amount of phosphine oxide and a tetramethyldisiloxane/titanium isopropoxide reductant system. Details are discussed in the Full Paper by M.-W. Ding et al. on page 2568 ff (DOI: 10.1002/ejoc.201601628).

One-pot and regioselective synthesis of 3,4-dihydroquinazolines by Sequential Ugi/Staudinger/aza-Wittig reaction starting from functionalized isocyanides

Co-reporter:Jun Xiong, Xiao Wei, Yan-Mei Yan, Ming-Wu Ding

Tetrahedron 2017 Volume 73, Issue 38(Issue 38) pp:

Publication Date(Web):21 September 2017

DOI:10.1016/j.tet.2017.08.011

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.Download high-res image (146KB)Download full-size image

Multifunctional odorless isocyano(triphenylphosphoranylidene)-acetates: synthesis and direct one-pot four-component Ugi/Wittig cyclization to multisubstituted oxazoles

Co-reporter:Zhi-Lin Ren;Zhi-Rong Guan;Han-Han Kong

Organic Chemistry Frontiers 2017 vol. 4(Issue 10) pp:2044-2048

Publication Date(Web):2017/09/26

DOI:10.1039/C7QO00490G

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.

Catalytic aza-Wittig Reaction of Acid Anhydride for the Synthesis of 4H-Benzo[d][1,3]oxazin-4-ones and 4-Benzylidene-2-aryloxazol-5(4H)-ones

Co-reporter:Long Wang, Yi-Bi Xie, Nian-Yu Huang, Jia-Ying Yan, Wei-Min Hu, Ming-Guo Liu, and Ming-Wu Ding

ACS Catalysis 2016 Volume 6(Issue 6) pp:4010

Publication Date(Web):May 16, 2016

DOI:10.1021/acscatal.6b00165

Compared to the aza-Wittig reaction of aldehydes, ketones, amides, and esters, the aza-Wittig reaction of acid anhydride was always overlooked, which should be an important part of Wittig reactions. Here, the aza-Wittig reaction of anhydride and catalytic aza-Wittig reaction of anhydride were both developed with high yields, which provides an efficient method to synthesize of 4H-benzo[d][1,3]oxazin-4-ones and 4-benzylidene-2-aryloxazol-5(4H)-ones. The strategy of copper-catalyzed reduction of phosphine oxide was used and found effective for this transformation. Additionally, the one-pot catalytic aza-Wittig reaction of carboxylic acids was achieved. Furthermore, NMR experiments and Hammett plot recorded the process of catalytic aza-Wittig reaction of anhydride, which provides direct proof that the copper-catalyzed reduction of waste phosphine oxide is the key step in this transformation.Keywords: anhydride; carboxylic acids; catalytic aza-Wittig reaction

One-pot synthesis of 1H-isochromenes and 1,2-dihydroisoquinolines by a sequential isocyanide-based multicomponent/Wittig reaction

Co-reporter:Long Wang, Zhi-Rong Guan and Ming-Wu Ding

Organic & Biomolecular Chemistry 2016 vol. 14(Issue 8) pp:2413-2420

Publication Date(Web):15 Jan 2016

DOI:10.1039/C5OB02405F

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.

New efficient synthesis of multisubstituted benzimidazoles and quinoxalin-2(1H)-ones by a Ugi 4CC/aza-Wittig sequence starting from aromatic amine precursors

Co-reporter:Yan-Mei Yan, Yun Gao, Ming-Wu Ding

Tetrahedron 2016 Volume 72(Issue 35) pp:5548-5557

Publication Date(Web):1 September 2016

DOI:10.1016/j.tet.2016.07.048

An efficient preparation of multisubstituted benzimidazoles and quinoxalin-2(1H)-ones by Ugi 4CC/aza-Wittig sequence was developed. The 2-azidobenzenamines, obtained from CH 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.

New efficient synthesis of isoquinoline-1,3(2H,4H)-diones and isoindolin-1-ones via sequential Ugi/cyclization reaction

Co-reporter:Ding Yuan, Zhuan Duan, Yong Rao, Ming-Wu Ding

Tetrahedron 2016 Volume 72(Issue 2) pp:338-346

Publication Date(Web):14 January 2016

DOI:10.1016/j.tet.2015.11.051

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.

One-Pot Synthesis of Multisubstituted Benzimidazoles via Sequential Ugi and Catalytic Aza-Wittig Reaction Starting from 2-Aminobenzoyl Azides

Co-reporter:Yan-Mei Yan, Yong Rao, and Ming-Wu Ding

The Journal of Organic Chemistry 2016 Volume 81(Issue 3) pp:1263-1268

Publication Date(Web):January 13, 2016

DOI:10.1021/acs.joc.5b02575

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.

Unexpected Synthesis of 5,6-Dihydropyridin-2(1H)-ones by a Domino Ugi/Aldol/Hydrolysis Reaction Starting from Baylis–Hillman Phosphonium Salts

Co-reporter:Xiao-Hua Zeng, Hong-Mei Wang, and Ming-Wu Ding

Organic Letters 2015 Volume 17(Issue 9) pp:2234-2237

Publication Date(Web):April 15, 2015

DOI:10.1021/acs.orglett.5b00849

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.

New efficient synthesis of 2,5,6-trisubstituted oxazolo[5,4-d]pyrimidi-7(6H)-ones via an oxazolyliminophosphorane

Co-reporter:Guo-Ping Zeng, Chang-Quan Cai, Fen Tan, Ming-Wu Ding

Chinese Chemical Letters 2015 Volume 26(Issue 9) pp:1158-1160

Publication Date(Web):September 2015

DOI:10.1016/j.cclet.2015.06.011

A new efficient synthesis of 2,5,6-trisubstituted oxazolo[5,4-d]pyrimidi-7(6H)-ones by consecutive aza-Wittig reaction was developed. The sequential three-component reaction of oxazolyliminophosphorane 4, isocyanates and amines produced 2,5,6-trisubstituted oxazolo[5,4-d]pyrimidi-7(6H)-ones 7 in good overall yields in the presence of catalytic amount of EtONa.A new efficient synthesis of 2,5,6-trisubstituted oxazolo[5,4-d]pyrimidi-7(6H)-ones by consecutive aza-Wittig reaction was developed.

Synthesis of 2,3-Dihydro-1H-2-benzazepin-1-ones and 3H-2-Benzoxepin-1-ones by Isocyanide-Based Multicomponent Reaction/Wittig Sequence Starting from Phosphonium Salt Precursors

Co-reporter:Long Wang, Zhi-Lin Ren, and Ming-Wu Ding

The Journal of Organic Chemistry 2015 Volume 80(Issue 1) pp:641-646

Publication Date(Web):December 3, 2014

DOI:10.1021/jo502275f

A one-pot synthesis of multisubstituted 2,3-dihydro-1H-2-benzazepin-1-ones and 3H-2-benzoxepin-1-ones by an I-MCR/Wittig sequence was developed. The reaction of phosphonium salt 3, arylglyoxals 4, amine 5 (or without), and isocyanide 6 produced the 2,3-dihydro-1H-2-benzazepin-1-ones 8 or 3H-2-benzoxepin-1-ones 10 in good yields via a sequential Ugi or Passerini condensation and intramolecular Wittig reaction in the presence of NEt3.

New efficient synthesis of 1H-pyrimido[2,1-b]quinazoline-2,6-diones via a tandem aza-Wittig/nucleophilic addition/intramolecular cyclization/isomerization reaction starting from the Baylis–Hillman adducts

Co-reporter:Ding Yuan, Han-Han Kong, Ming-Wu Ding

Tetrahedron 2015 Volume 71(Issue 3) pp:419-423

Publication Date(Web):21 January 2015

DOI:10.1016/j.tet.2014.12.006

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.

Reversible P(III)/P(V) Redox: Catalytic Aza-Wittig Reaction for the Synthesis of 4(3H)-Quinazolinones and the Natural Product Vasicinone

Co-reporter:Long Wang;Ying Wang;Min Chen

Advanced Synthesis & Catalysis 2014 Volume 356( Issue 5) pp:1098-1104

Publication Date(Web):

DOI:10.1002/adsc.201300950

One-pot regioselective synthesis of β-lactams by a tandem Ugi 4CC/SN cyclization

Co-reporter:Xiao-Hua Zeng, Hong-Mei Wang, Yan-Mei Yan, Lei Wu, Ming-Wu Ding

Tetrahedron 2014 70(23) pp: 3647-3652

Publication Date(Web):

DOI:10.1016/j.tet.2014.04.033

A simple and one-pot synthesis of 2,3,4,5-tetrasubstituted 4,5-dihydro-3H-1,4-benzodiazepines

Co-reporter:Ying Wang, Min Chen, Ming-Wu Ding

Tetrahedron 2013 69(43) pp: 9056-9062

Publication Date(Web):

DOI:10.1016/j.tet.2013.08.034

Efficient Regioselective Synthesis of 3-Iodoindole N-Carboximidamides and N-Carboximidoates by a Sequential Aza-Wittig/Iodine Induced Cyclization

Co-reporter:Yibo Nie;Zhuan Duan ;Mingwu Ding

Chinese Journal of Chemistry 2012 Volume 30( Issue 8) pp:1807-1812

Publication Date(Web):

DOI:10.1002/cjoc.201200281

Abstract

3-Iodoindole N-carboximidamides and N-carboximidoates 4 were prepared regioselectively via a sequential aza-Wittig/iodine induced cyclization, starting from easily accessible 2-alkynylphenyl iminophosphorane, isocyanates, various nucleophiles and iodine.

Unexpected synthesis of indolo[1,2-c]quinazolines by a sequential Ugi 4CC–Staudinger–aza-Wittig–nucleophilic addition reaction

Co-reporter:Ping He, Yi-Bo Nie, Jing Wu and Ming-Wu Ding

Organic & Biomolecular Chemistry 2011 vol. 9(Issue 5) pp:1429-1436

Publication Date(Web):17 Nov 2010

DOI:10.1039/C0OB00855A

A new sequential Ugi–Staudinger–aza-Wittig–nucleophilic addition reaction was developed to construct indolo[1,2-c]quinazoline derivatives, starting from the easily accessible 2-azidobenzaldehyde, carboxylic acid, 2-acylaniline and isocyanide. It is noteworthy that this is the first report of the cyclization of the Ugi adduct to give a dihydroindole ring system with two quaternary carbon centers, via the nucleophilic addition reaction of the methine group to the carbonyl group.

Efficient Synthesis of New Tetracyclic Benzofuro[3,2-d]-imidazo[1,2-a]pyrimidine-2,5-(1H,3H)-diones

Co-reporter:Yanggen Hu;Min Liu;Mingwu Ding

Chinese Journal of Chemistry 2010 Volume 28( Issue 2) pp:309-312

Publication Date(Web):

DOI:10.1002/cjoc.201090072

Abstract

The aza-Wittig reaction of iminophosphorane (1) with aromaic isocyanates gave carbodiimides (2), which were allowed to react further with (-amino ester in the presence of a catalytic amount of sodium ethoxide to give selectively new tetracyclic benzofuro[3,2-d]imidazo[1,2-a]pyrimidine-2,5-(1H,3H)-diones (5) in good yields. X-ray structure analysis of 5i verified the proposed structure and the reaction selectivity.

Iminophosphorane-mediated efficient synthesis of new tricyclic 3,5-dihydro-1,2,3-triazolo[4,5-d]-1,2,4-triazolo[1,5-a]pyrimidin-9-ones

Co-reporter:Jun-Feng Zhao, Chang Xie, Sheng-Zhen Xu, Ming-Wu Ding and Wen-Jing Xiao

Organic & Biomolecular Chemistry 2006 vol. 4(Issue 1) pp:130-134

Publication Date(Web):28 Nov 2005

DOI:10.1039/B513715B

The carbodiimides 2, obtained from aza-Wittig reactions of iminophosphorane 1 with aromatic isocyanates, reacted with hydrazine to give selectively 6-amino-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones 5. Compounds 5 were further transformed to iminophosphoranes 6 by reaction with triphenylphosphine, hexachloroethane and triethylamine. A tandem aza-Wittig reaction of iminophosphorane 6 with isocyanate or acyl chloride generated previously unreported 3,5-dihydro-1,2,3-triazolo[4,5-d]-1,2,4-triazolo[1,5-a]pyrimidin-9-ones 10 or 12 in satisfactory yield. X-ray structure analysis of 10g verified the proposed structure and the reaction selectivity.

New Facile Synthesis of 3,5-Dihydro-6H-imidazo[1,2-b]-1,2,4-triazol-6-ones by an Iminophosphorane-Mediated Annulation

Co-reporter:Ju-Zhen Yuan;Bo-Qiao Fu;Guang-Fu Yang

European Journal of Organic Chemistry 2006 Volume 2006(Issue 18) pp:

Publication Date(Web):19 JUL 2006

DOI:10.1002/ejoc.200600201

Iminophosphorane 1 reacted with an aromatic isocyanate to unexpectedly give a mixture of carbodiimides 2, 3 and 4 through both the normal and the abnormal aza-Wittig reactions. 3-Aminoimidazolone 10 was obtained from the reaction of hydrazine hydrate with carbodiimide 2. Reaction of 10 with triphenyphosphane, hexachloroethane and triethylamine produced iminophosphorane 11 in good yield. A tandem aza-Wittig reaction of iminophosphorane 11 with isocyanate or CS₂ generated 3,5-dihydro-6H-imidazo[1,2-b]-1,2,4-triazol-6-ones 13 or 15 in satisfactory yield. Carbodiimides 18, obtained from normal aza-Wittig reactions of vinyl iminophosphorane 17 with aromatic isocyanates, reacted with hydrazine to give 2-arylamino-3-amino-4H-imidazol-4-ones 20. One-pot reactions of 2-arylamino-3-amino-4H-imidazol-4-ones 20 with isocyanates (or acyl chlorides), triphenyphosphane, hexachloroethane and triethylamine produced 3,5-dihydro-6H-imidazo[1,2-b]-1,2,4-triazol-6-ones 22 (or 23) in good yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)