摘要:
2,3,4,5-Tetrasubstituted 4,5-dihydro-3H-1,4-benzodiazepines were synthesized in one-pot by a new sequential Ugi 4CC/Staudinger/aza-Wittig reaction, starting from easily accessible o-azidobenzaldehyde, alpha-amino ketone hydrochloride, isocyanide and carboxylic acid. (C) 2013 Elsevier Ltd. All rights reserved.
摘要:
Azides obtained from Baylis–Hillman adducts were treated with triphenylphosphine to give the corresponding iminophosphoranes that underwent aza-Wittig reactions with aryl isocyanates and then reacted with amines, alcohol, or phenols in the presence of catalytic amounts of sodium alkoxide or potassium carbonate to give the corresponding 2,3,5-trisubstituted pyrimidin-4(3H)-ones directly in good yields.
作者机构:
[Nie, Yi-Bo; Duan, Zhuan; Ding, Ming-Wu] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Ding, Ming-Wu] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, LuoYu Rd 100, Wuhan 430079, Peoples R China.
通讯机构:
[Ding, Ming-Wu] C;Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, LuoYu Rd 100, Wuhan 430079, Peoples R China.
摘要:
A series of 1,2,4-trisubstituted imidazoles 5 were synthesized efficiently by a tandem aza-Wittig/1,5-electrocyclic ring-closure reaction of vinyliminophosphoranes 3 with aldehydes. Reactions of 5s,t with triphenylphosphine produced iminophosphoranes 7. A tandem aza-Wittig reaction of iminophosphorane 7 with isocyanate generated imidazo[1,2-c]quinazolines 9 in high yields. (C) 2011 Elsevier Ltd. All rights reserved.
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2012年77(1):696-700 ISSN:0022-3263
通讯作者:
Ding, Ming-Wu
作者机构:
[Nie, Yi-Bo; Wang, Long; 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:
Carbodiimides 4, obtained from aza-Wittig reactions of iminophosphorane 3 with aryl isocyanates, reacted with secondary amines in the presence of a catalytic amount of sodium alkoxide to give 1,2,4,5-tetrasubstituted imidazoles 7 in good yields. However, 4-acylimidazoles 11 were obtained, as phenols were used in the presence of a catalytic amount of potassium carbonate due to further air oxidation of the expected products 10.
摘要:
Isothiocyanate 6, obtained from vinyliminophosphorane 4 with CS2, reacted with various aliphatic primary amines to afford directly the 1,4,5-trisubstituted imidazolidine-2-thiones 5. However, the reaction of isothiocyanate 6 with aliphatic secondary amines provided 2,4,5-trisubstituted thiazoles 10 in good yields.
摘要:
1H-Pyrazolo[1,5-b]indazoles were prepared via a domino Staudinger–aza-Wittig cyclization in one-pot fashion, starting from easily accessible azides and triphenylphosphine.
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2012年77(6):2954-2958 ISSN:0022-3263
通讯作者:
Ding, Ming-Wu
作者机构:
[Xie, Hai; Ding, Ming-Wu; Yuan, Ding] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Xie, Hai] Shanxi Datong Univ, Coll Chem & Chem Engn, Datong 037009, Shanxi, 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:
2,4,5-Trisubstituted oxazoles 6 were unexpectedly prepared from a tandem reaction of vinyliminophosphorane 3 with various acyl chlorides in a one-pot fashion.
摘要:
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.
摘要:
The crystal structure of the title compound 1-(4-fluorophenyl)-2-hexylthio-benzo [4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidin-5(1H)-one(C23H_21FN4O2S, Mr=436.5)has been prepared and determined by single-crystal X-ray diffraction. The crystal is of monoclinic, space group P21/n with a=13.9854(3),b=17.2678(4),c=18.1828(5)A,β=99.364(2)°,V=4332.58(18) A~ 3,Z=4, Dc=1.338,F(000)=1824,μ=0.185 mm~(-1), MoKa radiation(λ=0.71073),R=0.0538 and wR=0.1162 for 4728 observed reflections with I>2σ(I).X-ray diffraction analysis reveals the fused rings of benzo[4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidin-5(1H)-one system are nearly coplanar. The crystal packing is mainly stabilized by weak intermolecular C-H…O hydrogen bond andπ-πinteractions
作者机构:
[Wang, Long; Zhong, Ying; 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 series of 2,3,4-trisubstituted 3,4-dihydroquinazoline 3 was prepared by intramolecular aza-Wittig reaction of amide carbonyl groups with methyldiphenyl iminophosphorane, which was obtained from a Ugi 4CC/Staudinger sequence. Further intramolecular Heck reaction of 3d'-g' in the presence of catalytic amount of Pd(OAc)(2) gave 6,12-dihydroindolo[2,1-b]quinazolines 4a-d in good yields. (C) 2011 Elsevier Ltd. All rights reserved.
摘要:
The title compound (C20H18FN3O2, Mr = 351.37) is prepared and its crystal structure is determined by single crystal X-ray diffraction. The crystal is tetragonal, the P-42(1)c space group with a = 11.0922(6) Å, b = 11.0922(6) Å, c = 28.6271(15) Å, V = 3522.2(3) Å3, Z = 8, d
x
= 1.325 g/cm3, F(000) = 1472, μ = 0.095 mm−1, MoK
α radiation (λ = 0.71073), R = 0.0505, wR = 0.1090 for 2433 observed reflections with I > 2σ(I). The X-ray diffraction analysis reveals that all ring atoms in the benzo[4,5]furo[3,2-d]pyrimidinone moieties are almost coplanar.