Preparation of O-, S- and N-Benzyl Derivatives of 1,6-Anhydro-β-D-hexopyranoses via Aziridine Ring Opening

2002 ◽  
Vol 67 (12) ◽  
pp. 1805-1819 ◽  
Author(s):  
Jiří Kroutil ◽  
Jindřich Karban ◽  
Tomáš Trnka ◽  
Miloš Buděšínský ◽  
Miloslav Černý
Keyword(s):  
Benzyl Alcohol ◽  
Ring Opening ◽  
Intramolecular Rearrangement ◽  
Aziridine Ring ◽  
Derivatives Of

The aziridine ring opening of N-tosylepimino carbohydrates 1-6 having D-allo, D-manno, D-galacto and D-talo configurations with benzyl alcohol, benzylamine and phenylmethanethiol afforded 2-, 3- and 4-O-benzyl-, benzylsulfanyl and benzylamino derivatives of 1,6-anhydro-β-D-hexopyranoses of D-gluco, D-galacto and D-manno configurations 7-23 in 44-99% yields. Hexenopyranoses 24-26 were prepared from tosylepimino carbohydrates 1, 4 and 5 by intramolecular rearrangement of the aziridine ring.

Synthesis of trifluoromethyl γ-aminophosphonates by nucleophilic aziridine ring opening

2015 ◽  
Vol 13 (39) ◽  
pp. 10050-10059 ◽  
Author(s):  
T. Cytlak ◽  
M. Saweliew ◽  
M. Kubicki ◽  
H. Koroniak
Keyword(s):  
Ring Opening ◽  
Aziridine Ring ◽  
Ring Opening Reactions ◽  
Derivatives Of

The synthesis of phosphonated derivatives of trifluoromethyl aziridines by two methods and their application in ring opening reactions have been demonstrated.

Preparation of O-, S- and N-Benzyl Derivatives of 1,6-Anhydro-β-D-hexopyranoses via Aziridine Ring Opening.

ChemInform ◽  
2003 ◽  
Vol 34 (23) ◽  
Author(s):  
Jiri Kroutil ◽  
Jindrich Karban ◽  
Tomas Trnka ◽  
Milos Budesinsky ◽  
Miloslav Cerny
Keyword(s):  
Ring Opening ◽  
Aziridine Ring ◽  
Derivatives Of

Cleavage of the Epimines of 1,6-Anhydrohexoses with Fluoride Anion

2005 ◽  
Vol 70 (12) ◽  
pp. 2075-2085 ◽  
Author(s):  
Jiří Kroutil ◽  
Klára Jeništová
Keyword(s):  
Fluoride Anion ◽  
Ring Cleavage ◽  
Protecting Group ◽  
Reaction Conditions ◽  
Aziridine Ring ◽  
Cleavage Reactions ◽  
Derivatives Of ◽  
Fluoro Derivatives

Aziridine ring cleavage reactions of five N-nosylepimines (2-6) having D-talo, D-galacto, D-manno, and D-allo configurations with potassium hydrogendifluoride under various reaction conditions have been performed. The cleavage regioselectively afforded diaxial isomers of vicinal amino-fluoro derivatives of 1,6-anhydro-β-D-gluco- and mannopyranose 7-11 in 51-94% yields. Removal of 2-nitrobenzenesulfonyl protecting group with benzenethiol has been attempted in the case of compound 10.

scholarly journals Intramolecular N–Me and N–H aminoetherification for the synthesis of N-unprotected 3-amino-O-heterocycles

2021 ◽  
Author(s):  
Mahesh P. Paudyal ◽  
Mingliang Wang ◽  
Juha H. Siitonen ◽  
Yimin Hu ◽  
Muhammed Yousufuddin ◽  
...  
Keyword(s):  
Ring Opening ◽  
Domino Reaction ◽  
Aziridine Ring

A mild Rh-catalyzed method for synthesis of cyclic unprotected N–Me and N–H 2,3-aminoethers using an olefin aziridination–aziridine ring-opening domino reaction has been developed.

Derivatives of isatin in aqueous solution. I. Kinetics of ring opening of Isatin-5-sulfonate

1981 ◽  
Vol 34 (2) ◽  
pp. 365 ◽  
Author(s):  
H Stunzi
Keyword(s):  
Ring Opening ◽  
Rate Of Change ◽  
Spectroscopic Methods ◽  
Ph Values ◽  
Buffer Region ◽  
Pka Value ◽  
Back Titration ◽  
Kinetics Of ◽  
Derivatives Of ◽  
Sulfonate Anion

The reactions of isatin-5-sulfonate anion (si-) which cause a hysteresis in pH titrations were studied by pH-metric and n.m.r, spectroscopic methods. Rapid alkalimetric titrations [I 0.15 M (KNO3),37�] gave the pKa value corresponding to the addition of OH- to si- [pKa(ring) 9.55]. The slow ring opening to the sulfonatoisatate dianion (sia2-) led to a drift of the pH values towards an equilibrium buffer region. Its pKa, value [pKa(eq) 3.44] corresponds to the reaction si-+H2O ↔ sia 2-+H+ Rapid back-titration gave the pKa value of the ring-opened species Hsia- [pKa(open) c. 1.3]. The rate law for the ring opening d[sia]/dt=k2 [siOH](OH)+k1*[si] was obtained from the rate of change of pH. N-Methylisatin-5-sulfonate behaves analogously.

Stereoselective Syntheses of 4-Oxa Diaminopimelic Acid and Its Protected Derivatives via Aziridine Ring Opening

2007 ◽  
Vol 9 (21) ◽  
pp. 4211-4214 ◽  
Author(s):  
Hongqiang Liu ◽  
Vijaya R. Pattabiraman ◽  
John C. Vederas
Keyword(s):  
Ring Opening ◽  
Diaminopimelic Acid ◽  
Aziridine Ring ◽  
Stereoselective Syntheses

scholarly journals Fates of imine intermediates in radical cyclizations of N-sulfonylindoles and ene-sulfonamides

2015 ◽  
Vol 11 ◽  
pp. 1649-1655 ◽  
Author(s):  
Hanmo Zhang ◽  
E Ben Hay ◽  
Stephen J Geib ◽  
Dennis P Curran
Keyword(s):  
Carbonyl Group ◽  
Ring Opening ◽  
Radical Cyclizations ◽  
Type Reaction ◽  
Primary Products ◽  
Lactam Carbonyl Group ◽  
Lactam Carbonyl ◽  
Imine Reduction ◽  
Derivatives Of

Two new fates of imine intermediates formed on radical cyclizations of ene-sulfonamides have been identified, reduction and hydration/fragmentation. Tin hydride-mediated cyclizations of 2-halo-N-(3-methyl-N-sulfonylindole)anilines provide spiro[indoline-3,3'-indolones] or spiro-3,3'-biindolines (derived from imine reduction), depending on the indole C2 substituent. Cyclizations of 2-haloanilide derivatives of 3-carboxy-N-sulfonyl-2,3-dihydropyrroles also presumably form spiro-imines as primary products. However, the lactam carbonyl group facilitates the ring-opening of these cyclic imines by a new pathway of hydration and retro-Claisen-type reaction, providing rearranged 2-(2'-formamidoethyl)oxindoles.

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