Synthesis of .beta.-lactams from substituted hydroxamic acids

Miller, Marvin J.; Mattingly, Phillip G.; Morrison, Marjorie A.; Kerwin, James F.

doi:10.1021/ja00543a021

Cited by 156 publications

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“…A high degree of convergence in functionality and sense of chirality can thus be achieved with the intended target while utilizing the same number of required carbon atoms (Scheme 2). Ring closure by intramolecular attack of the amine nitrogen with a suitable leaving group on the hydroxyl terminus, as previously demonstrated for p-halopropionamides (7) or related derivatives (3)(4)(5), would complete the task of assembling the diminutive yet important synthetic intermediate. In spite of the seemingly trivial nature of this exercise, it should be noted that racemization, elimination, and intramolecular reactions could effectively compete with ring closure (5) and loom as major threats to such a strategy.…”

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confidence: 89%

“…Since the emergence of the monobactam family of monocyclic p-lactam antibiotics (1, 2) much effort has been devoted to their total synthesis (3)(4)(5), particularly since they have demonstrated potent antibacterial activity and high stability toward p-lactamases (6). Several reports have also been concerned with the synthesis of Zoxo-azetidines (7), 4-substituted-2-azetidinones (8), 2-amino-4-substituted-2-azetidinones (9), and related compounds (10).…”

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confidence: 99%

“…19). This method leads to ' Presented in part at the Xth European Symposium on Heterocyclic Chemistry, Kaiserslautern, Germany, Oct. [2][3][4]1984. See also ref.…”

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confidence: 99%

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Design and reactivity of organic functional groups—utility of imidazolylsulfonates in the synthesis of monobactams and 3-amino nocardicinic acid

Hanessian¹,

Couture²,

Wyss³

1985

Can. J. Chem.

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confidence: 89%

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confidence: 99%

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Design and reactivity of organic functional groups—utility of imidazolylsulfonates in the synthesis of monobactams and 3-amino nocardicinic acid

Hanessian¹,

Couture²,

Wyss³

1985

Can. J. Chem.

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“…Um outro procedimento bastante empregado para a obtenção destes compostos envolve a reação de um iminoéter (na forma de seu sal hidroclorídrico) ou um ortoéster com β-aminoálcoois 12,13 (Esquema 3). Várias outras metodologias de obtenção de 2-oxazolinas podem ser encontradas na literatura como as que utilizam hidroxiamidas [14][15][16][17] e eneamidas [18][19][20] como material de partida, além de processos envolvendo amidotelurinilação de alcenos 21 , abertura de epóxidos [22][23][24] , abertura de N-acilaziridinas 25 , reação de aldeídos com isocianetos 26 , reações pericíclicas [27][28][29] , entre outras.…”

Section: Esquema 1 Esquema 2 Esquemaunclassified

2-oxazolinas quirais: algumas aplicações como indutores de assimetria em reações orgânicas

Oliveira¹,

Simonelli²,

Marques³

et al. 1999

Quím. Nova

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foi desenvolvida uma metodologia alternativa, utilizando os mesmos precursores, a qual permite a obtenção de tais compostos à temperatura ambiente 10 (Esquema 2).Um dos primeiros artigos de revisão publicados enfocando oxazolinas dava ênfase à utilização industrial de tais compostos os quais vinham sendo empregados como aditivos de gasolina e óleos lubrificantes, inibidores de corrosão e nas indústri-as têxtil, farmacêutica e fotográfica, entre outras aplicações 1 . A partir do final da década de 60, a exemplo do que vinha ocorrendo com outros heterociclos como as ditianas 2 , oxazinas 3 e isoxazóis 4 , a reatividade das 2-oxazolinas começou a ser mais intensamente investigada, abrindo boas perspectivas para um crescente emprego de tais compostos em síntese orgânica [5][6][7][8] . Neste artigo serão abordadas algumas reações que se processam com estereosseletividade empregando 2-oxazolinas quirais como indutores de assimetria, além de uma breve introdução sobre métodos de obtenção de 2-oxazolinas e a discussão de algumas de suas propriedades, tendo em vista que a utilização de tais sistemas, em nível nacional, tem sido pouco explorada. Métodos de obtenção de 2-oxazolinasO sistema 2-oxazolínico é conhecido desde 1884 9 e a metodologia de preparação mais simples e direta envolve a reação de ácidos carboxílicos com β-amino álcoois sob aquecimento e com remoção de água (Esquema 1).Essa metodologia encontra limitações pois exige o uso de altas temperaturas não sendo compatível quando se emprega amino álcoois mais voláteis ou quando se faz presente funções mais sensíveis à condição reacional necessária. Desta forma Esquema 1 Esquema 2Esquema 3

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“…[1][2][3][4][5][6][7][8] ROOC-N_N-COOR + Ph 3 P + R OH + Nu : → Nu-R + Ph 3 PO + ROOC-NH-NH-COOR Cyclic compounds are formed when the alcohol molecule contains a suitably placed nucleophile. Epoxides are obtained from acyclic 1,2-diols under the Mitsunobu conditions 9 and from cyclic trans-1,2-diols.…”

Section: Introductionmentioning

confidence: 99%

Convenient preparation of carbonyl compounds from 1,2-diols utilizing Mitsunobu conditions

Barrero¹,

Álvarez-Manzaneda²,

Chahboun³

2000

Tetrahedron Letters

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Abstract1,1-Disubstituted 1,2-diols are efficiently converted into carbonyl compounds by reaction with triphenylphosphine and diethyl azodicarboxylate. © 2000 Elsevier Science Ltd. All rights reserved.Keywords: Mitsunobu reactions; diols; aldehydes.The Mitsunobu reaction is a useful synthetic tool which allows the conversion of an alcohol function into a wide variety of functional groups. [1][2][3][4][5][6][7][8] ROOC-N_N-COOR + Ph 3 P + R OH + Nu : → Nu-R + Ph 3 PO + ROOC-NH-NH-COOR Cyclic compounds are formed when the alcohol molecule contains a suitably placed nucleophile. Epoxides are obtained from acyclic 1,2-diols under the Mitsunobu conditions 9 and from cyclic trans-1,2-diols. [10][11][12][13] Under the same conditions triphenylphosphoranes resulted from cyclic cis-1,2-diols. [11][12][13][14] Methyl shikimate (8a), having cis-and trans-diol groups, leads to the corresponding epoxide 8b, under these conditions. 15 During our research on the synthesis of bioactive compounds from labdane diterpenes we have found that diol 12a is transformed with excellent yield into drimenal (12b) 16 when it is treated with triphenylphosphine (TPP) and diethyl azodicarboxylate (DEAD) in benzene. In order to elucidate the scope and synthetic application of this reaction the behaviour of a variety of 1,2-diols with these reagents has been studied. The results obtained are summarized in Table 1 and compared with those previously reported. As may be seen, monosubstituted and disubstituted 1,2-diols are converted into epoxides or phosphoranes, depending on whether the hydroxyl groups adopt an antiperiplanar (cyclic trans-diols and acyclic diols) or an eclipsed conformation (cis-diols), respectively. The formation of phosphorane 3b from diol 3a can be attributed to the bulky dioxolane groups which prevent the hydroxyl groups from adopting the anti disposition. 1,1-Disubstituted-1,2-diols lead to the formation of aldehydes or ketones, depending on whether the less substituted carbon is primary or secondary. Even acyclic 1,1-disubstituted * Corresponding author.

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Synthesis of .beta.-lactams from substituted hydroxamic acids

Cited by 156 publications

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Design and reactivity of organic functional groups—utility of imidazolylsulfonates in the synthesis of monobactams and 3-amino nocardicinic acid

Design and reactivity of organic functional groups—utility of imidazolylsulfonates in the synthesis of monobactams and 3-amino nocardicinic acid

2-oxazolinas quirais: algumas aplicações como indutores de assimetria em reações orgânicas

Convenient preparation of carbonyl compounds from 1,2-diols utilizing Mitsunobu conditions

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