Reactions of phthalic anhydride with 2-amino alcohols

Wicks, Zeno W.; Chen, Gang-Fung

doi:10.1021/jo01322a011

Cited by 14 publications

(5 citation statements)

References 2 publications

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“…When AMP and BTCA were reacted [Fig. 3(C)], the amine bending mode disappeared, and a new band around 1643 cm −1 , corresponding to the amide stretching mode, appeared 43. On the other hand, the band corresponding to the carbonyl stretching mode of BTCA shifted slightly to a higher wave number.…”

Section: Resultsmentioning

confidence: 99%

Multifunctional cotton fabric: Antimicrobial and durable press

Cerkez

Kocer

Worley

et al. 2011

J of Applied Polymer Sci

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2-Amino-2-methyl-1-propanol (AMP) was coated onto cotton fabric with 1,2,3,4-butanetetracarboxylic acid (BTCA) as a crosslinking agent to simultaneously impart antimicrobial and durable-press functionalities. The coatings were characterized and confirmed by attenuated total reflectance-IR and thermogravimetric analysis. The coated fabrics were rendered biocidal upon exposure to dilute household bleach, and the chlorinated swatches exhibited about 6 log reductions of Escherichia coli O157:H7 and Staphylococcus aureus within 5 min of contact time. A concentration of 1.5 wt % AMP was sufficient to produce this biocidal efficacy. Increasing the BTCA content of the coating improved the wrinkle recovery angle. The coatings were very stable toward repeated laundering, and they exhibited sufficient halogen storage stabilities for industrial applications. A photolytic decomposition was observed when the coatings were exposed to UVA light.

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Section: Resultsmentioning

confidence: 99%

Multifunctional cotton fabric: Antimicrobial and durable press

Cerkez

Kocer

Worley

et al. 2011

J of Applied Polymer Sci

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“…However, the 0-activated N-phthalimide-protected (S)-phenylalaninol 3b, which was readily accessible by standard procedures [9] [lo], did not furnish a phosphino derivative 2 upon reaction with KPPh, in T H E Instead, one single unique product was isolated after workup and chromatography, and, to our surprise, it was elucidated to be the (epoxymethano)-bridged tetracyclic lactam 7 (Scheme 3). A mechanistic rationale postulates again an intramolecular S, reaction; however, in this case, a carbonyl 0-atom replaces the OTos leaving group.…”

Section: R=boc B R=tosmentioning

confidence: 98%

An Unusual Acyliminium Cyclization and Other Drawbacks during an Attempted Synthesis of a Chiral Primary α‐Phosphinoalkanamine

Christoffers

1998

Helvetica Chimica Acta

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Studies towards the synthesis of a chiral primary a-phosphinoalkanamine la are reported. 0-Activated, N-carbamate-protected phenylalaninol 3a did not undergo S, reaction with KPPh, : instead, after N-dcprotonation, intramolecular substitution led to formation of the aziridine derivative 5a (Sdirmne 2). N-Phthalimido-protected, 0-activated phenylaloninol 3b also underwent an intramolecular process on treatment with KPPh,, i.c., an unusual aryl-acyliminium cyclization furnishing the (epoxymethano)isoindolo[l,2-cr]isoquinolinone 7 (Schcinc~ 3). In it reaction with KPPh,, the N,N-dibenzyl-protected and activated phenylalaninol3d finally yielded the intermolecular S, reaction product 2a (Schemr4). However, debenzylation by catalytic hydrogenation turned out to be iinpossible.Introduction. ~ Asymmetric C,C-bond-forming reactions are of great significance for the synthesis of optically active compounds, and towards this goal, the application of chiral transition-metal catalysts has become a flourishing field of research. Chelating phosphine ligands are particularly suited for the coordination to late transition metals due to their n-acceptor character, and the preparation of chiral representatives from the readily available starting materials of the chiral pool is an attractive and popular strategy. For example, Kumada and coworkers [I] have introduced the N,N-dimethyl-cc-phosphinoalkanamines ( = p-(dimethy1amino)alkylphosphines) of the general type 1 (Scheme I ) , which originate from natural cc-amino acids, and which have been shown to be highly efficient ligands for catalytic asymmetric Grignard cross-coupling reactions applying Ni" or Pd" [2]. In our eyes, the synthesis of analogues like l a bearing a primary-amine function seemed to be also an attractive goal. The latter ligands were planned to be applied in our projects on transition-metal-catalyzed Michael reactions [3]. Moreover, the presence of the primary amino group should also allow an application as a chiral auxiliary, e g . , after amide or aminocarbene complex [4] formation. A retrosynthetic

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“…No acyl shi of amide 1-AE to ester 3-AE was detected in this case (Scheme 12). 115 Hassanzadeh's group in 2017 supplied cyclic imides. In the rst step, PA (1) reacted with glycinamide (26) in freshly distilled and dried pyridine under reux conditions to yield the corresponding amic acid (27) within 5 h. The amic acid underwent ring closure with acetic anhydride and anhydrous sodium acetate to form imides (28, 29), which were isolated via column chromatography (Scheme 13).…”

Section: Applications Of Pa In Twocomponent Reactionsmentioning

confidence: 99%