Studies on lactams. Part 65. N-Unsubstituted .beta.-lactams from .beta.-hydroxy-.alpha.-amino acids. Facile preparation of intermediates for isocephalosporins

1982 ◽  
Vol 47 (21) ◽  
pp. 4075-4081 ◽  
Author(s):  
Ajay K. Bose ◽  
M. S. Manhas ◽  
J. E. Vincent ◽  
K. Gala ◽  
I. F. Fernandez
Keyword(s):  
Amino Acids ◽  
Beta Lactams ◽  
Facile Preparation

scholarly journals Facile preparation of optically pure [?-2H]-?-amino acids

1992 ◽  
Vol 14 (4) ◽  
pp. 269-274 ◽  
Author(s):  
Shui-Tein Chen ◽  
Chen-Chen Tu ◽  
Kung-Tsung Wang
Keyword(s):  
Amino Acids ◽  
Facile Preparation ◽  
Optically Pure

A versatile synthetic route to 1,5-dithiocins from o-mercapto aromatic aldehydes

1999 ◽  
Vol 77 (1) ◽  
pp. 113-121 ◽  
Author(s):  
Ian WJ Still ◽  
Rosanne Natividad-Preyra ◽  
F Dean Toste
Keyword(s):  
Amino Acids ◽  
Primary Amine ◽  
Methyl Esters ◽  
Aromatic Aldehydes ◽  
Primary Amines ◽  
Synthetic Route ◽  
General Reaction ◽  
Limited Success ◽  
Facile Preparation ◽  
General Method

An earlier procedure for the facile preparation of benzo-fused 1,5-dithiocins 2a-2c from o-mercapto- benzaldehydes has been improved and shown to be capable of extension to the preparation of several naphthalene-derived analogues. The general method also afforded several N-alkylated 1,5-dithiocins 4, 5 by replacing NH3 with the appropriate primary amine. It was found that N-acylation of the 1,5-dithiocins was successful only with methyl chloroformate. Attempted N-phenylation met with limited success but was shown to be unnecessary since even the less reactive aniline readily undergoes the general reaction of primary amines. When simple α-amino acids, or their methyl esters, were employed as the primary amine in the reaction with o-mercaptobenzaldehyde, the formation of the N-alkylated 1,5-dithiocins 4a, 17a,17b with accompanying loss of -COOH or -COOMe was observed, in preparatively useful yields. A mechanism is proposed for this interesting transformation.Key words: 1,5-dithiocins, α-amino acids, N-acylation, decarboxylation.

scholarly journals Amino Acids and Peptides. XXXV. Facile Preparation of p-Nitroanilide Analogs by the Solid-Phase Method.

2000 ◽  
Vol 48 (11) ◽  
pp. 1740-1744 ◽  
Author(s):  
Keiko HOJO ◽  
Mitsuko MAEDA ◽  
Shin IGUCHI ◽  
Timothy SMITH ◽  
Hiroshi OKAMOTO ◽  
...  
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Phase Method ◽  
Solid Phase Method ◽  
Facile Preparation

scholarly journals A one-pot synthesis of .BETA.-lactams by the reaction of .BETA.-haloacyl chlorides with .ALPHA.-amino acids.

1982 ◽  
Vol 30 (5) ◽  
pp. 1574-1578 ◽  
Author(s):  
TADASHI OKAWARA ◽  
TAKASHI MATSUDA ◽  
YOSHIHIDE NOGUCHI ◽  
MITSURU FURUKAWA
Keyword(s):  
Amino Acids ◽  
Beta Lactams ◽  
One Pot ◽  
One Pot Synthesis

scholarly journals Preparation of α-amino acids via Ni-catalyzed reductive vinylation and arylation of α-pivaloyloxy glycine

2021 ◽  
Vol 12 (1) ◽  
pp. 220-226
Author(s):  
Xianghua Tao ◽  
Yanchi Chen ◽  
Jiandong Guo ◽  
Xiaotai Wang ◽  
Hegui Gong
Keyword(s):  
Amino Acids ◽  
Reductive Coupling ◽  
Facile Preparation

We have developed Ni-catalyzed reductive coupling of N-carbonyl protected α-pivaloyloxy glycine with Csp2-electrophiles that enabled facile preparation of α-amino acids, including those bearing hindered branched vinyl groups.

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