1,3-Dipolar cycloaddition reactions of imines of α-amino-acid esters: X-ray crystal and molecular structure of methyl 4-(2-furyl)-2,7-diphenyl-6,8-dioxo-3,7-diazabicyclo[3.3.0]octane-2-carboxylate

Grigg, Ronald; Kemp, J A; Sheldrick, George M.; Trotter, J.

doi:10.1039/c39780000109

Cited by 91 publications

(37 citation statements)

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“…The condensation between the amino acid and isatin followed the pathway outlined in Scheme 2 to yield, after decarboxylation, the azomethine ylide 8 that, in the presence of a dipolarophile, gave rise to the pyrrolidine-2-spiro-3Ј-oxindoles 10. It is possible to generate an azomethine ylide via thermal tautomerisation of imines, [17] but in these reactions the azomethine ylide was not obtained by such a process.…”

Section: N-unsubstituted α-Amino Acidsmentioning

confidence: 99%

The Three‐Component Reaction between Isatin, α‐Amino Acids, and Dipolarophiles

2004

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Section: N-unsubstituted α-Amino Acidsmentioning

confidence: 99%

The Three‐Component Reaction between Isatin, α‐Amino Acids, and Dipolarophiles

2004

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“…When (4) is applied in the same conditions, only 149 quartets are estimated negative with Pc = 0.95. NEWQB [Grigg, Kemp, Sheldrick & Trotter (1978); C24HEoN205, P1, Z = 4; Neq : 124]. 343 quartets are estimated negative by (3), with Pc = 0.64.…”

Section: L=p++p - Zs=(r~r2±rar4)/n 1/2 Z~ = ( R~r3 + R2r4)/ N ~/2 mentioning

confidence: 99%

On the reliability of quartet estimates

Altomare¹,

Burla²,

Cascarano³

et al. 1993

Acta Cryst Sect A

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“…Three intramolecular condensation pathways may be proposed for regioisomeric cis-5-arylpyrrolidine-2,3,4-tricarboxylic acid monoamides V and VI: (i) [4,2]-condensation in isomer V, leading to 3,6-diazabicyclo[3.2.1]octane derivative; (ii) [4,3]condensation in isomer V with formation of octahydropyrrolo[3,4-c]pyrrole structure; and (iii) [3,2]-condensation in VI with formation of octahydropyrrolo[3,4-b]-pyrrole skeleton (Fig. 3).…”

Section: Methodsmentioning

confidence: 99%

“…10.1134 There are some published data on the synthesis of compounds I via generation of 1,3-dipole A from the corresponding N-alkylidene derivatives of α-amino acid esters on heating above 100°C for a long time [3][4][5]. We recently developed an organocatalytic procedure for 1,3-dipolar cycloaddition of activated di-PYRROLIDINE-2,3,4-TRICARBOXYLIC ANHYDRIDES: I.…”

mentioning

confidence: 98%

Pyrrolidine-2,3,4-tricarboxylic anhydrides: I. Organocatalytic synthesis and fusion of pyrrole ring by the action of p-fluorobenzylamine

2011

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N-Boc-glycine effectively catalyzes 1,3-dipolar cycloaddition of maleic anhydride to N-benzylidene α-amino acid esters, which leads to the formation of pyrrolidine-2,3,4-tricarboxylic anhydrides. The subsequent opening of the anhydride fragment in the adducts by the action of p-fluorobenzylamine is regioselective, and it involves recyclization to produce polysubstituted octahydropyrrolo [3,4-b]pyrroles. The newly synthesized fused pyrrolidines inhibit enzymatic activity of thrombin (factor IIA) in vitro.Consecutive and/or joint modification of the above functional groups in molecules I could lead to various complex low-molecular organic compounds. Heterocyclic anhydrides I are isostructural to cantharidin (II, R = Me) and norcantharidin (II, R = H). Cantharidin is produced as protecting agent by various beetle species, and it exhibits a broad spectrum of antitumor activity and inhibits serine/threonine protein phosphatases; the same is also typical of its synthetic analog, norcantharidin [1]. Opening of the anhydride ring in compounds II and their analogs by the action of nitrogenPolyfunctional organic compounds attract considerable interest from the viewpoint of creation of combinatorial libraries for biological screening. Pyrrolidine-2,3,4-tricarboxylic acid 3,4-anhydrides I may be regarded as promising molecular structures possessing various functional groups. Compounds like I contain three functional groups: a secondary amino group, anhydride fragment, and carboxy (ester) group. centered nucleophiles gives dicarboxylic acid monoamides or imides which show modified biological activity as compared to parent compounds [1,2]. The goal of the present work was to develop an effective procedure for the synthesis of heterocyclic anhydrides I, examine their reactions with primary amines, and test the products thus obtained for inhibitory activity toward thrombin (factor IIA).Functionalized pyrrolidines I can be synthesized by 1,3-dipolar cycloaddition of maleic anhydride to azomethine ylides A as shown in Scheme 1.

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1,3-Dipolar cycloaddition reactions of imines of α-amino-acid esters: X-ray crystal and molecular structure of methyl 4-(2-furyl)-2,7-diphenyl-6,8-dioxo-3,7-diazabicyclo[3.3.0]octane-2-carboxylate

Abstract: Die Imino‐ester (I) liefern mit (II), (IV) und (VI) die Cycloaddukte (III), (V) bzw. (VII) und (VIII).

Cited by 91 publications

References 0 publications

The Three‐Component Reaction between Isatin, α‐Amino Acids, and Dipolarophiles

The Three‐Component Reaction between Isatin, α‐Amino Acids, and Dipolarophiles

On the reliability of quartet estimates

Pyrrolidine-2,3,4-tricarboxylic anhydrides: I. Organocatalytic synthesis and fusion of pyrrole ring by the action of p-fluorobenzylamine

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