The nucleophilic addition/ring closure (NARC) sequence for the stereocontrolled synthesis of heterocycles

1997 ◽  
pp. 87-101 ◽  
Author(s):  
Patrick Perlmutter
Keyword(s):  
Nucleophilic Addition ◽  
Ring Closure ◽  
Stereocontrolled Synthesis

scholarly journals Alicyclic β- and γ-Amino Acids: Useful Scaffolds for the Stereocontrolled Access to Amino Acid-Based Carbocyclic Nucleoside Analogs

Molecules ◽  
2019 ◽  
Vol 24 (1) ◽  
pp. 161
Author(s):  
Attila Márió Remete ◽  
Loránd Kiss
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Nucleoside Analogs ◽  
Ring Closure ◽  
Amino Ester ◽  
Nucleophilic Displacement ◽  
Stereocontrolled Synthesis ◽  
Key Steps ◽  
Carbocyclic Nucleoside ◽  
Formed Adduct

Stereocontrolled synthesis of some amino acid-based carbocyclic nucleoside analogs containing ring C=C bond has been performed on β- and γ-lactam basis. Key steps were N-arylation of readily available β- or γ-lactam-derived amino ester isomers and amino alcohols with 5-amino-4,6-dichloropyrimidine; ring closure of the formed adduct with HC(OMe)3 and nucleophilic displacement of chlorine with various N-nucleophiles in the resulting 6-chloropurine moiety.

scholarly journals Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines

2019 ◽  
Vol 2019 ◽  
pp. 1-7 ◽  
Author(s):  
N. F. Kirillov ◽  
E. A. Nikiforova ◽  
D. V. Baibarodskikh ◽  
T. A. Zakharova ◽  
L. S. Govorushkin
Keyword(s):  
Nitrogen Atom ◽  
Carbonyl Group ◽  
Nucleophilic Addition ◽  
Ring Closure ◽  
Amide Nitrogen ◽  
Ester Carbonyl ◽  
Ester Carbonyl Group ◽  
Amide Nitrogen Atom

Interaction of the Reformatsky reagents, prepared from methyl 1-bromocyclopentane-1-carboxylate or methyl 1-bromocyclohexane-1-carboxylate, with N,N′-bis(arylmethylidene)benzidines has given rise to a set of intermediates as a result of nucleophilic addition to the C=N group of a substrate. Further intramolecular attack of the amide nitrogen atom onto the ester carbonyl group is responsible for the ring closure, which affords two series of spirocompounds: 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.4]octan-1-one) or 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.5]nonan-1-ones).

A Nucleophilic Addition Ring Closure [NARC]-Based Synthesis of (+)-Nonactic Acid.

ChemInform ◽  
2003 ◽  
Vol 34 (20) ◽  
Author(s):  
Benjamin Fraser ◽  
Patrick Perlmutter
Keyword(s):  
Nucleophilic Addition ◽  
Ring Closure

Addition initiated ring closure: synthesis of substituted spiro[2.4]hepta-4,6-dienes via cyclopentadiene intermediates from fulvene precursors

1984 ◽  
Vol 62 (11) ◽  
pp. 2451-2455 ◽  
Author(s):  
Kazimierz Antczak ◽  
John F. Kingston ◽  
Alex G. Fallis
Keyword(s):  
Intramolecular Cyclization ◽  
Nucleophilic Addition ◽  
Ring Closure

The reactivity of the epoxy-fulvene 1, prepared by pyrrolidine catalyzed condensation of cyclopentadiene and epoxybutanone, has been examined with various nucleophiles. It is a versatile intermediate for the preparation of spiro[2.4]hepta-4,6-diene synthons via nucleophilic addition to the C6 position of the fulvene followed by intramolecular cyclization of the substituted cyclopentadiene anion generated insitu.

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