Reactions of dehydroacetic acid and related pyrones with secondary amines

Stephen, J. F.; Marcus, E.

doi:10.1021/jo01261a011

Cited by 11 publications

(4 citation statements)

References 3 publications

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“…The formation of 8 can be envisaged by an intramolecular cyclocondensation assisted by aliphatic amines. The formation of this type of compound has been already reported by heating DHA in the presence of several aliphatic and aromatic amines [30].…”

Section: Resultsmentioning

confidence: 94%

Synthesis and reactivity of 6‐methyl‐4H‐furo[3,2c]pyran‐3,4‐dione

Hikem-Oukacha

Rachedi

Hamdi

et al. 2010

Journal of Heterocyclic Chem

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An efficient synthesis of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one by bromination of dehydroacetic acid in glacial acetic acid is described. Novel 4‐hydroxy‐6‐methyl‐3‐(2‐substituted‐thiazol‐4‐yl)‐2H‐pyran‐2‐ones have been prepared from the reaction of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one with thioamides, thiourea, and diphenylthiocarbazone. The condensation reaction of 6‐methyl‐4H‐furo[3,2c]pyran‐3,4‐dione, obtained from the reaction of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one with aliphatic amines, with benzaldehydes and acetophenones led to novel 2‐arylidene‐6‐methyl‐2H‐furo[3,2‐c]pyran‐3,4‐diones and 6‐(2‐arylprop‐1‐enyl)‐2H‐furo[3,2‐c]pyran‐3,4‐diones. The structure of all compounds was established by elemental analysis, IR, NMR, and mass spectra. J. Heterocyclic Chem., 2011.

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Section: Resultsmentioning

confidence: 94%

Synthesis and reactivity of 6‐methyl‐4H‐furo[3,2c]pyran‐3,4‐dione

Hikem-Oukacha

Rachedi

Hamdi

et al. 2010

Journal of Heterocyclic Chem

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“…With these possibilities for nucleophilic opening in mind, bis-coupled pyrone 19 was treated with a variety of nucleophiles (see the Supporting Information for all the attempted nucleophiles) . Among the nucleophiles that were investigated, we observed our first successful ring-opening upon treating 19 with cyclic amines . As outlined in Scheme b, morpholine opened 19 in a 1,6-fashion to furnish the decarboxylated enamine 20 , which was isolated in 83% yield as a single diastereomer.…”

Section: Resultsmentioning

confidence: 99%

A Unified Strategy for the Enantiospecific Total Synthesis of Delavatine A and Formal Synthesis of Incarviatone A

2019

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We describe a symmetry-inspired synthetic approach that has enabled a short synthesis of delavatine A and a formal synthesis of incarviatone A, which are two likely biosynthetically related natural products. The indane core of these natural products was constructed through a cascade sequence involving five transformations that occur in a single pot. Leveraging symmetry has allowed us to trace both natural products back to a versatile building block, 3,5-dibromo-2pyrone, and studies related to site-selective cross-coupling of this polyhalogenated heterocycle are described. In addition, our strategy gave access to a putative biogenetic precursor, from which the syntheses of both natural products were attempted.

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“…The low field signal for the NH group proton is at 15.93 ppm in the PMR spectrum of compound (IV) which points in favor of such a ring. Compounds formed by reacting 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one with amines [5,6] may exist in two tautomeric forms (a and b). Based on certain PMR and IR spectra the authors of [6] expressed a preference for form b.…”

Section: In the Present Work The Dihydrazide (Ii) Was Isolated From Tmentioning

confidence: 99%

Synthesis and structure of dihydrazones obtained from the dihydrazide of S,S′-(1,3,4-thiadiazole-2,5-diyl)bis(2-mercaptopropionic acid)

Rutavichyus¹,

Valyulene²

1998

Chem Heterocycl Compd

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It has been established by PMR spectroscopy that dihydrazones obtained by the condensation of the dihydrazide of S,S'-(l,3,4-thiadiazole-2,5-diyl)bis(2-mercaptopropionic acid) with aldehydes, ketone.s, and B-dicarbonyl compounds exist in solution as a mixture of stercoisomeric forms, the ratio of which depends on the structure of the carbonyl compound used in the condensation. E',Z'-conformational (twisting) isomerism due to hindered rotation about an N--CO amide bond and E,Zgeometric syn-and anti-isomerism relative to a C=N bond in bisacyl hydrazone derivatives of 2-mercaptoacetic acid have already been studied by us [1, 2]. However, there are no data in the literature on hydrazones of or-substituted 2-mercaptoacetic acid. With the aim of filling the gap existing in this area we have synthesized and studied the structure 9 f dihydrazones from the dihydrazide of S,S'-(1,3,4-thiadiazole-2,5-diyl)bis(2-mercaptopropionic acid). In the present work the dihydrazide (II) was isolated from the condensation of S,S'-(1,3,4-thiadiazole-2,5-diyl)bis(2-mercaptopropionic acid) dimethyl ester (I) with liydrazine hydrate in 2-propanol. Compound (II) reacts with aldehydes or ketones to form bisacyl hydrazones (IIIa-1), (IV), and (V) (Scheme 1).Scheme 1 llla-j R 1 = H, 1 R t = CH3; a R 2 = 2,3-(MeO)2C6H3; b R 2 = 2,4-(HO) 2C6H3; c R 2 = 2-HO-3-Me0C6H3; dR 2 = 4-(Me)2NC6H4; e'R 2 = 4-CIC6H4; f R 2 = 3-NO2C6H4; g R 2 = 2-BrC6H4; h R 2 ~ 3,4-(OCH20)C6H3; i R 2 = C4H30; j R 2 = 5-(Me)2NC4H20; kR l =R 2 = C3H7; I R 2 = 3,4-(OCH20)C6H3CH2

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Reactions of dehydroacetic acid and related pyrones with secondary amines

Cited by 11 publications

References 3 publications

Synthesis and reactivity of 6‐methyl‐4H‐furo[3,2c]pyran‐3,4‐dione

Synthesis and reactivity of 6‐methyl‐4H‐furo[3,2c]pyran‐3,4‐dione

A Unified Strategy for the Enantiospecific Total Synthesis of Delavatine A and Formal Synthesis of Incarviatone A

Synthesis and structure of dihydrazones obtained from the dihydrazide of S,S′-(1,3,4-thiadiazole-2,5-diyl)bis(2-mercaptopropionic acid)

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