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.
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.
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2014年80(1):641-646 ISSN:0022-3263
通讯作者:
Ding, Ming-Wu
作者机构:
[Wang, Long; Ding, Ming-Wu; Ren, Zhi-Lin] 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 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.
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.
摘要:
The catalytic aza-Wittig reaction based on a phosphine/phosphine oxide catalytic cycle is reported. The by-product triphenylphosphine oxide (Ph3PO) was reduced in situ to triphenylphosphine (Ph3P) with good chemselectivity so that the aza-Wittig reaction can be accomplished by using merely a catalytic amount of triphenylphosphine. The reaction has been demonstrated in an efficient synthesis of 4(3H)-quinazolinones and the natural product (S)-vasicinone in high yields, by using a catalytic amount of triphenylphosphine (5%) and the tetramethyldisiloxane/titanium tetraisopropoxide [TMDS/Ti(O-i-Pr)(4)] reductant system (81-95% yields and >99% ee).
摘要:
beta-Lactam scaffold was fabricated regioselectively by a facile one-pot base-mediated synthesis. The reactions of bromoacetic acid 1, primary amines 2, isocyanides 3, and arylglyoxals 4 produced 2-aroyl-4-oxoazetidine-2-carboxamides 6 in good yields via a one-pot tandem Ugi condensation and intramolecular C-alkylation at room temperature in the presence of Cs2CO3. (C) 2014 Elsevier Ltd. All rights reserved.
摘要:
A one-pot base-mediated synthesis of 5-oxopyrrolidine-2-carboxamides was developed. The reaction of Baylis–Hillman bromides 1, primary amines 2, isocyanides 3 and arylglyoxals 4 produced the 5-oxopyrrolidine-2-carboxamides 6 in good yields via a tandem Ugi condensation and intramolecular substitution at room temperature in the presence of Cs2CO3.
摘要:
5H-Indazolo[3,2-b]-1,3,4-benzotriazepines were directly prepared by the reaction of azides with triphenylphosphine via a tandem aza-Wittig cyclization in good yields.
摘要:
The title compound N-(2-(1-butyl-3-phenylureido)-1H-indol-3-yl)-N-(4-chlorophenyl)-benzamide (C_(32)H_(29)ClN_4O_2, Mr = 537.04) was synthesized by a sequential Ugi four component condensation (4CC)/aza-Wittig/carbodiimide-mediated cyclization, and the structure was characterized by NMR, IR, MS, elemental analysis and X-ray single-crystal diffraction analysis. The crystal belongs to orthorhombic, space group P2_12_12_1 with a = 11.3663(9), b = 13.3248(10), c =18.7887(15) A, V = 2845.6(4) A~3, Z = 4, D_c = 1.254 mg/m~3, μ = 0.170 mm~(-1), F(000) = 1128, the final R = 0.0538 and wR = 0.1187. X-ray analysis reveals that the new five-membered ring (C(14)-C(15)-N(2)-C(16)-C(21)) and the benzene ring (C(16)-C(21)) are nearly coplanar.