Transformation of Amines and N-Heteroarylformamidines into Esters of Substituted b-Amino-a,b-dehydro-a-amino Acids

Stanovnik, B.; Svete, Julij; Tišler, M.; Zorz, Lilijana; Hvala, Anastazija; Simonič, Igor

doi:10.3987/com-87-4418

Cited by 48 publications

(30 citation statements)

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“…1). 8 X-ray analyses have been carried out for compound 1 and some of its derivatives, including dipeptides,9 and for compound 5,7 showing that in the solid state the orientation of both substituted amino groups around the double bond in both compounds is Z. However, in solution, the presence of another isomer and/or rotamer has been observed in some instances.…”

Section: Introductionmentioning

confidence: 99%

NMR Studies of Substituted 2,3-Diaminopropenoates

Grdadolnik

Stanovnik

1997

Magn. Reson. Chem.

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Section: Introductionmentioning

confidence: 99%

NMR Studies of Substituted 2,3-Diaminopropenoates

Grdadolnik

Stanovnik

1997

Magn. Reson. Chem.

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“…The formation of these conjugated systems is favourable for the cycloreversion. The above method affords a new synthesis of the tricyclic systems 4 and 7 6 and illustrates the general scope and importance and the applicability to obtain fused heterocycles via the RDA technique. This procedure does not require the flash vacuum pyrolysis applied in traditional RDA reactions.…”

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confidence: 82%

Double Retro Diels-Alder Reaction Applied for Preparation of a Pyrimido[1,2-b]pyridazine

Miklós

Stájer

Sohar

et al. 2000

Synlett

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Boiling diendo-or diexo-2-aminobicyclo[2.2.1]hept-5ene-3-carbohydrazides 1 with 3-aroylnorbornenecarboxylic acid 2 in toluene yielded the pyrimido[1,2-b]pyridazine 4 directly in a double retro Diels-Alder process. Similarly, the reaction of anthranilic hydrazide 5 and 2 furnished the tricyclic benzo-fused analogue 7 via a single cycloreversion. The principle of the new method applied: the reactants were built up on cyclopentadienes and the dienes were cleaved by heating after condensation to furnish hetero bicyclic compound.

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“…14−16 However, in some instances, the intermediates 7 cyclized in the presence of sodium methoxide 15 to fused pyrimidones such as 9. 14−16 However, in some instances, the intermediates 7 cyclized in the presence of sodium methoxide 15 to fused pyrimidones such as 9.…”

Section: Figurementioning

confidence: 99%

Alkyl 2-Substituted 3-(Dimethylamino)propenoates and Related Compounds - Versatile Reagents in Heterocyclic Chemistry

2000

Synlett

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Alkyl 2-substituted 3-(dimethylamino)propenoates and related compounds, masked a-formyl-a-amino-and a-formyl-a-hydroxy acid derivatives, available in one step from 2-substituted acetic acid derivatives by treatment with amide acetals, represent a useful synthetic tool for a simple preparation of various heterocyclic systems and aryl-and heteroaryl substituted amino acid derivatives. On the other hand, 3-(dimethylamino)propenoates can also serve as reagents for the protection of amino group, e. g. in peptide synthesis. Protection of Amino Group 4.10 Transformations of Chiral 3-(Dimethylamino)propenoate Analogs 5Conclusion

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Transformation of Amines and N-Heteroarylformamidines into Esters of Substituted b-Amino-a,b-dehydro-a-amino Acids

Cited by 48 publications

References 0 publications

NMR Studies of Substituted 2,3-Diaminopropenoates

NMR Studies of Substituted 2,3-Diaminopropenoates

Double Retro Diels-Alder Reaction Applied for Preparation of a Pyrimido[1,2-b]pyridazine

Alkyl 2-Substituted 3-(Dimethylamino)propenoates and Related Compounds - Versatile Reagents in Heterocyclic Chemistry

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