Reaction of mesoionic compounds deriving from cyclic N-acyl-α-aminoacids with N-(phenylmethylene)benzenesulfonamide

被引:17
作者
Dalla Croce, P
Ferraccioli, R
La Rosa, C
机构
[1] Fac Farm, Ist Chim Organ, I-20133 Milan, Italy
[2] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[3] Ctr CNR, I-20133 Milan, Italy
关键词
D O I
10.1016/S0040-4020(98)01026-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We studied the behaviour of bicyclic mesoionic compounds derived from the cyclodehydration of cyclic N-acyl-alpha-aminoacids 1-4 with N-(phenylmethylene)benzenesulfonamide 5. The reaction affords spirocyclic beta-lactams and/or imidazo-condensed products (the 1,3-dipolar cycloaddition adducts) depending on the experimental conditions and on the nature of the substituent R on the mesoionic ring. (C) 1998 Elsevier Science Ltd. All rights reserved.
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收藏
页码:201 / 210
页数:10
相关论文
共 15 条
[1]   SYNTHESIS AND ANTILEUKEMIC ACTIVITY OF 5-SUBSTITUTED 2,3-DIHYDRO-6,7-BIS(HYDROXYMETHYL)-1H-PYRROLIZINE DIESTERS [J].
ANDERSON, WK ;
COREY, PF .
JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (06) :812-818
[2]  
APPLEWHITE TH, 1959, J AM CHEM SOC, V81, P2212
[3]   N,N-DIMETHYLCHLOROSULFITEMETHANIMINIUM CHLORIDE (SOCL2-DMF) A VERSATILE DEHYDRATING REAGENT [J].
ARRIETA, A ;
AIZPURUA, JM ;
PALOMO, C .
TETRAHEDRON LETTERS, 1984, 25 (31) :3365-3368
[4]   2-CHLOROACRYLONITRILE AS A CYCLODIPOLAROPHILE IN 1,3-CYCLOADDITIONS - 3-CYANOPYRROLES [J].
BENAGES, IA ;
ALBONICO, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (22) :4273-4276
[5]   A DIRECT SYNTHESIS OF DL-BAIKIAIN [J].
BURGSTAHLER, AW ;
AIMAN, CE .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (04) :489-492
[6]   CHIRAL LIGANDS CONTAINING HETEROATOMS .13. OPTICALLY-ACTIVE 4-(2'-PYRIDYL)-1,3-OXAZOLIDINES - AN IMPROVED SYNTHESIS OF 2-(2'-PYRIDYL)-2-AMINOALCOHOLS [J].
CONTI, S ;
COSSU, S ;
GIACOMELLI, G ;
FALORNI, M .
TETRAHEDRON, 1994, 50 (47) :13493-13500
[7]  
DALLACROCE P, 1995, TETRAHEDRON, V51, P9385
[8]   THE ESTER ENOLATE IMINE CONDENSATION ROUTE TO BETA-LACTAMS [J].
HART, DJ ;
HA, DC .
CHEMICAL REVIEWS, 1989, 89 (07) :1447-1465
[9]   A CONTRIBUTION TO THE CONFUSION SURROUNDING THE REACTION OF KETENES WITH IMINES TO PRODUCE BETA-LACTAMS - A COMPARISON OF STEREOSELECTIVITY DEPENDENCE ON THE METHOD OF KETENE GENERATION - ACID CHLORIDE TRIETHYLAMINE VS PHOTOLYSIS OF CHROMIUM CARBENE COMPLEXES [J].
HEGEDUS, LS ;
MONTGOMERY, J ;
NARUKAWA, Y ;
SNUSTAD, DC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (15) :5784-5791
[10]   SYNTHESIS OF BETA-(TRIFLUOROMETHYL)PYRROLES VIA THE CYCLOADDITION OF MUNCHNONES TO ELECTRON-DEFICIENT TRIFLUOROMETHYLATED OLEFINS [J].
OKANO, T ;
UEKAWA, T ;
MORISHIMA, N ;
EGUCHI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5259-5262