A simple and general one-pot synthesis of some 2h-pyran-2-ones and fused pyran-2-ones

doi:10.1016/S0040-4020(01)89774-X

Tetrahedron

Volume 46, Issue 6, 1990, Pages 2081-2088

https://doi.org/10.1016/S0040-4020(01)89774-X Get rights and content

Abstract

A general one-pot synthesis of some 2H-pyran-2-ones and fused pyran-2-ones starting from 1,3-dlcarbonyl compounds, N-acylglycines and one-carbon synthons (trialkyl orthoformates, diethoxymethyl acetate or N,N-dlmethylformamide dimethyl acetal) in acetic anhydride (or in a mixture of acetic anhydride and acetic acid) is described.

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Cited by (58)

Diels-Alder reactions of 1-amino-1,3-dienes and related systems
2021, Tetrahedron
Citation Excerpt :
Amino-2H-pyran-2-ones also behave as electron-rich cyclic 1-aminodienes in DA reactions. The preparation and DA reactions of α-amino-2H-pyran-2-ones have been studied by Kočevar's group extensively [170–183]. Fused 2H-pyran-2-ones 294 reacted with maleimides in boiling decalin during ca. 9 h providing fused isoindole derivatives 297 (Scheme 72) [175].
In this account, Diels-Alder reactions of different 1-amino-1,3-dienes with dienophiles are considered. As 1-amino-1,3-dienes, dienamines, dienamides, 1,2-dihydropyridines, 2-pyridones and vinylic heterocycles, such as vinyl-pyrroles, pyrazoles, imidazoles, indoles, tetrahydropyridines and dihydropyridones are studied. As dienophiles, enals, acrylic, maleic and fumaric derivatives, quinones, tetracyanoethylene, dialkyl acetylenedicarboxylates, nitroolefins, nitrosobenzene and azocompounds play an important role. Synthetic applications of these inter or intramolecular, racemic or enantioselective reactions in order to prepare polycyclic nitrogen-containing heterocycles, are pointed out, specially in the preparation of naturally occurring and biologically active compounds mainly alkaloids. The most significant feature of the chemistry described in this account is the fact that this methodology represents a simple and selective way to get N-containing heterocyclic compounds in only one reaction step, creating at least two carbon-carbon bonds in a regio-, diastereo- and enantioselective fashion.
2H-Pyran-2-ones and their annelated analogs as multifaceted building blocks for the fabrication of diverse heterocycles
2017, Tetrahedron
Citation Excerpt :
The base induced ring transformation of 4-sec.amino-2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitriles109 by stirring with indane-2-one in the presence of sodium hydride in dry THF for 12 h at room temperature. Purification of the crude product delivered (Z)-(2-chloro-6H-indeno[2,1-b]thiochromeno[4,3-d]pyran-7(9H)-ylidene)acetonitrile 496,289 Scheme 210. Various approaches for the fabrication of spiranes suffering from limitations of functional group incompatibility and restriction to substitution pattern, so efforts to search newer, economical and facile route did not diminish.
2H-Pyran-2-ones are widely present in nature and found as either isolated or in fused form. Depending on the fusion of benzene ring, pyran can give coumarins, isocoumarins, dibenzopyrans etc. This class of molecules exhibit excellent biological activity and photophysical properties. Apart from these, 2H-pyran-2-one also acts as very good Michael acceptor, therefore act as very important synthetic precursor. Suitably functionalized 2H-pyran-2-one has been widely explored for their synthetic potential. In this review, we have focused on use of different nucleophiles based on carbon, nitrogen, oxygen and sulfur to generate vast molecular diversity. The functionalized 2H-pyran-2-ones exhibit three electrophilic centres with different electrophilicity. Use of suitable nucleophiles can act on either of the position based on its reactivity to generate new chemical entity. 2H-Pyran-2-one has been explored as precursor for the synthesis of various biologically important nucleuses like pyridine, pyrimidine, quinolines, isoquinolines, fused quinolines, pyrazole, pyrroles, imidazopyridine, thiazole, oxazole, fused and isolated pyrans, coumarins, isocoumarins, benzothiophenes, dibenzohiophenes, dibenzofurans, diazapines, oxahelicines, thia-oxa helicines, and various other heterocycles under base mediated conditions. Use of suitably substituted 2H-pyran-2-one and nucleophile can generate new molecular entity. In this review, we have discussed the properties, synthesis and their synthetic applications to generate various classes of heterocycles.
Comparison of the reaction pathways and intermediate products of a microwave-assisted and high-pressure-promoted cycloaddition of vinyl-moiety-containing dienophiles on 2H-pyran-2-ones
2011, Tetrahedron
A comparative study of the reaction pathway of the cycloaddition of various vinyl-containing dienophiles on a set of substituted 3-acylamino-2H-pyran-2-ones under microwave-assisted and high-pressure conditions is presented. In the course of the reaction both the intermediate products, i.e., the 2-oxabicyclo[2.2.2]oct-5-ene (the exo/endo selectivity depended upon the dienophile) and the alkoxycyclohexadiene systems, were isolated and comprehensively characterized; this included X-ray diffraction analyses. The role of the base (DABCO) as an organocatalyst was further elucidated.
An expeditious synthesis of β-pyrimidyl-α,β-didehydro-α-amino acid derivatives and pyrano[2,3-d]pyrimidines using microwave-assisted conditions
2009, Tetrahedron
An expeditious transformation of 5-acyl-2H-pyran-2-ones with various amidines as 1,3-binucleophiles into isomerically pure (E)-α,β-didehydro-α-amino acid derivatives (DDAAD) containing the 5-pyrimidyl moiety at the β-position is described. The method was performed in ethanolic (or ethanol/water) solutions in the presence of Na₂CO₃ as a nontoxic base and under microwave-assisted conditions. When starting from the 5-ethoxycarbonyl-2H-pyran-2-one derivative and in the presence of DBU as a base the corresponding pyrano[2,3-d]pyrimidines were prepared.
An expedient route to indoles via a cycloaddition/cyclization sequence from (Z)-1-methoxybut-1-en-3-yne and 2H-pyran-2-ones
2008, Tetrahedron
The cycloaddition of (Z)-1-methoxybut-1-en-3-yne (2) with 5,6-disubstituted 3-acylamino-2H-pyran-2-ones 1 under microwave-irradiation conditions, with classical heating or at high-pressures (13–15 kbar) affords the benzene derivatives 3 with a strategically positioned 2-methoxyethenyl moiety. In some cases, at high-pressures after long reaction times, 2,2-dimethoxyethyl products 4 were obtained. Adducts 3 and 4 can be cyclized under mild conditions into 1,5,6-trisubstituted indole derivatives 5.
Ring transformations of 2H-pyran-2-ones and fused pyran-2-ones with nucleophilic reagents
2009, Heterocycles

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A simple and general one-pot synthesis of some 2h-pyran-2-ones and fused pyran-2-ones

Abstract

Tetrahedron

Tetrahedron Lett.

J. Org. Chem.

Chem. Ber.

Synthesis

Yakagaku Zasshi