Synthesis of 1,2‐disubstituted isoindoles from o‐phthalaldehyde and primary amines

Nan'ya, S.; Tange, Toshiaki; Maekawa, E.

doi:10.1002/jhet.5570220248

Cited by 25 publications

(11 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…They exhibit signals both of isoindol and isoindoline, the latter being consistent with those of compounds III and IV . The interpretation and spectral data are in agreement with the compound having the same skeleton (but different substitution) prepared from OPA and an amine in a different way .…”

Section: Resultssupporting

confidence: 82%

“…The reaction of phthalaldehyde [= ortho ‐phthalaldehyde (OPA)] with amines was generally studied several times already . This reaction is significant among others from the analytical point of view because the analysis of amino acids in biological samples (e.g., in food) is based on the reaction of a primary amine group with OPA to form fluorescent species .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Reaction of Phthalaldehyde with Aminoethanol under Different Conditions: Products and Mechanisms of Their Formation

Klíma

Polášek

Ludvı́k

et al. 2012

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Analysis of amino acids and very efficient disinfection procedures are based on the reaction of phthalaldehyde (OPA) with primary amines. In this contribution, aminoethanol (=kolamin) as a nitrogen‐containing nucleophile was used for the investigation of its reaction mechanism with OPA performed in basic aqueous buffered media (pH 9.5), where an influence of hydration or solvation is expected, and in anhydrous acetonitrile. Depending on the detailed reaction conditions, seven products were isolated and their structures determined by NMR, mass spectrometry, and X‐ray structure analysis. Reaction mechanisms are proposed, which involve hydride transfers to OPA (Cannizzaro‐type reaction).

show abstract

Section: Resultssupporting

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Reaction of Phthalaldehyde with Aminoethanol under Different Conditions: Products and Mechanisms of Their Formation

Klíma

Polášek

Ludvı́k

et al. 2012

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…The reactions of OPA with primary amines, which were carried out by Winter (1900) and Thiele & Schneider (1909) for the first time, have been broadly applied for the synthesis of important heterocyclic compounds with biological relevance. A number of such reactions have been investigated recently and several structures of condensation products have been reported (DoMinh et al, 1977;Nan'ya et al, 1985;Takahashi et al, 1996Takahashi et al, , 2004Takahashi et al, , 2005Takahashi & Hatanaka, 1997). However, the reaction mechanism is still not fully understood.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of 2-tert-butyl-2,3-dihydro-1H-benzo[c]pyrrol-1-one

et al. 2017

View full text Add to dashboard Cite

The asymmetric unit of the title compound, C 12 H 15 NO, comprises two symmetry-independent molecules which differ mainly in the conformations of the tert-butyl groups. The molecules contain an essentially planar five-membered 3-pyrroline ring incorporating a carbonyl substituent (pyrrolinone) which forms part of an isoindolinone skeleton. The planarity of the pyrrole ring is compared to other structures with isoindolinone. There are only weak intra-and intermolecular C-HÁ Á ÁO and C-HÁ Á Á-electron-ring interactions in the crystal structure.

show abstract

“…In addition to these applications, the reactions of OPA with primary amines, which were carried out by Thiele & Winter (1900) and Thiele & Schneider (1909) for the first time, are broadly applied for the synthesis of important heterocyclic compounds with biological relevance. A number of such reactions have been investigated recently and several structures of condensation products have been reported (DoMinh et al, 1977;Nan'ya et al, 1985;Takahashi et al, 1996Takahashi et al, , 2004Takahashi et al, , 2005Takahashi & Hatanaka, 1997), however, the reaction mechanism is still not fully understood.…”

Section: Introductionmentioning

confidence: 99%

A study of the planarity of the pyrrolone fragment in 2-isopropyl-2,3-dihydro-1H-isoindol-1-one

et al. 2016

View full text Add to dashboard Cite

Orthophthalaldehyde (o-phthalaldehyde, OPA) is an aromatic dialdehyde bearing two electron-withdrawing carbonyl groups. The reactions of OPA with primary amines are broadly applied for the synthesis of important heterocyclic compounds with biological relevance. A number of such reactions have been investigated recently and several structures of condensation products have been reported, however, the complex reaction mechanism is still not fully understood and comprises concurrent as well as consecutive reactions. The reaction products depend on the primary amine which reacts with OPA, the reaction environment (solvent) and the proportion of the reactants. The title molecule, C11H13NO, the product of the reaction of OPA with isopropylamine, contains a five-membered pyrrole C4N ring with a carbonyl substituent, which forms part of the isoindolinone unit. Though this pyrrole ring contains one C atom in the sp(3)-hybridized state, it is fairly planar. The title molecule has been compared with similar structures retrieved from the Cambridge Structural Database in order to study this phenomenon. The planarity of this fragment has been explained by the presence of partially delocalized C-C, C-N and C-O bonds, and by an inner angle in the planar pentagonal ring (∼108°), which is close to the ideal tetrahedral value for the sp(3)-hybridized state of the constituent C atom. Due to this propitious angle, this C atom can be present in states intermediate between sp(3)- and sp(2)-hybridized in different structures, while still maintaining the planarity of the ring. There are only weak intermolecular C-H...O hydrogen bonds and C-H...π-electron ring interactions in the structure. In particular, it is the pyrrole ring which is involved in these interactions.

show abstract

Synthesis of 1,2‐disubstituted isoindoles from o‐phthalaldehyde and primary amines

Cited by 25 publications

References 7 publications

Reaction of Phthalaldehyde with Aminoethanol under Different Conditions: Products and Mechanisms of Their Formation

Reaction of Phthalaldehyde with Aminoethanol under Different Conditions: Products and Mechanisms of Their Formation

Crystal structure of 2-tert-butyl-2,3-dihydro-1H-benzo[c]pyrrol-1-one

A study of the planarity of the pyrrolone fragment in 2-isopropyl-2,3-dihydro-1H-isoindol-1-one

Contact Info

Product

Resources

About