Reaction of 5-Hydroxyimino-1,3-dioxine-4,6-dione (Isonitroso Meldrum's Acid) with Carbodiimides to Give Parabanic Acids

Katagiri, Nobuya; Mori­shita, Yohei; Kaneko, Chikara

doi:10.3987/com-97-s58

Cited by 16 publications

(29 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Yield: 64% (250 mg). 1 H and 13 C NMR spectra of compound 16 matched with the literature reports. 20 HETEROCYCLES, Vol.…”

Section: 6-bis(bromomethyl)-2'2'-dimethyl-13-dihydrospiro[indene-25'-...supporting

confidence: 80%

Functionalization of Meldrum’s Acid by Diels‒Alder Approach

Kotha¹,

Gaikwad²

2022

HETEROCYCLES

View full text Add to dashboard Cite

We have synthesized several Meldrum's acid derivatives using Diels-Alder reaction as a key step. Here, the key sultine derivative is prepared by rongalite and the sultine derivative is useful as a latent diene.Meldrum's acid, 2,2-dimethyl-1,3-dioxane-4,6-dione, a cyclic ester, with an acidic CH2 group with pKa 4.83 1,2 is valuable synthon to design heterocycles and polycycles. 3 It is widely used in multicomponent reactions. 4 Meldrum's acid derivatives are also beneficial to assemble natural products and also used for synthesis of reactive intermediates and polymers. 5 They are also used in aza-Diels-Alder reaction with different dienophiles. 6 Uracil derivatives 7 are synthesized from trifloroacetyl Meldrum's acid. Gillena and co-workers 8 recently synthesized an antimicrobial compounds from Meldrum's acid. Various Meldrum's acid derivatives 1-5, shown in Figure 1 are useful in designing diverse polycycles. 9-18 Figure 1. Meldrum's acid derivatives used in organic synthesisRecently, Kotha and co-workers reported diverse Meldrum's acid derivatives involving a [2+2+2] cycloaddition reaction as a key step. Compound 4 undergo ring-closing metathesis (RCM) to generate cyclopentene derivative 6. Whereas, dialkyne derivative 5 and monoalkyne 7 undergo cyclotrimerization to generate the dibromo compound 8 with the aid of Mo(CO)6 (Scheme 1) under microwave irradiation conditions in acetonitrile. 19,20 Furthermore, we developed a new route for the synthesis of tetrahydroisoquinoline carboxylic acid derivatives via a [2+2+2] cyclotrimerization. 21,22 In view of our

show abstract

“…Yield: 64% (250 mg). 1 H and 13 C NMR spectra of compound 16 matched with the literature reports. 20 HETEROCYCLES, Vol.…”

Section: 6-bis(bromomethyl)-2'2'-dimethyl-13-dihydrospiro[indene-25'-...supporting

confidence: 80%

Functionalization of Meldrum’s Acid by Diels‒Alder Approach

Kotha¹,

Gaikwad²

2022

HETEROCYCLES

View full text Add to dashboard Cite

show abstract

“…15 Several other earlier reports described the formation of cyanoformamides. 16–21 For instance, hydration of cyanogen under high pressure using excess water gave 1-cyanoformamide, 16 whereas reaction of 5-hydroxyimino-1,3-dioxine-4,6-dione (isonitroso Meldrum's acid) with carbodiimides ( N , N ′-dicyclohexylcarbodiimide and N , N ′-diisopropylcarbodiimide) gave N -cyclohexylcyanoformamide and N -isopropylcyanoformamide, respectively. 17 Some other reagents like tetracyanoethylene, 18 5-tosyloxyimino-2,2-dimethyl-1,3-dioxane-4,6-dione, 19 4-chloro-5 H -1,2,3-dithiazol-5-one, 20 tetraalkyl-cyanoformamidinium salt, 21 or dichlorosulfenyl chlorides 22 have been employed in the synthesis of similar types of synthetic compounds.…”

Section: Introductionmentioning

confidence: 99%

Iodine-DMSO mediated conversion of N-arylcyanothioformamides to N-arylcyanoformamides and the unexpected formation of 2-cyanobenzothiazoles

et al. 2022

View full text Add to dashboard Cite

show abstract

“…78 The chemistry of this intermediate has been studied extensively by Katagiri and co-workers. [78][79][80][81][82][83][84][85] When the pyrolysis is carried out in solution (refluxing toluene), the nitrosoketene 150 can be trapped by [3+2] cycloaddition 86 with ketones to give the nitrones 151 (rather than the isomeric [4+2] products 152, c.f. Scheme 36).…”

Section: Figurementioning

confidence: 99%

“…Reactions of 147 with carbodiimides give intermediate adducts 153 which collapse at room temperature to the cyano-compounds 154 (Scheme 35). 85…”

Section: Figure 10mentioning

confidence: 99%

Synthetic Applications of the Pyrolysis of Meldrum's Acid Derivatives

Gaber¹,

McNab²

2001

Synthesis

View full text Add to dashboard Cite

The pyrolysis of Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) 1 derivatives in solution and in the gas-phase takes place by loss of acetone and carbon dioxide to provide ketene intermediates. In particular, methylene Meldrum's acid derivatives 7 often provide methyleneketenes 8, which act as substrates for internal hydrogen transfer leading to cyclisation reactions. The availability of versatile synthetic routes to 7 (in particular R = heteroatom) has led to the efficient preparation of a diverse range of cyclic compounds such as quinolinones, 3-hydroxythiophenes, naphthols, azepin-3(2H)-ones or pyrrolizin-3-ones initiated respectively by 1,3-1,4-1,5-1,6-or 1,7-prototropic shifts. These reactions are discussed in the context of a rigorous understanding of the chemistry of the ketene intermediates involved. Most of the work was published in the period 1980-2000 but important references to earlier literature are also included.

show abstract

Reaction of 5-Hydroxyimino-1,3-dioxine-4,6-dione (Isonitroso Meldrum's Acid) with Carbodiimides to Give Parabanic Acids

Cited by 16 publications

References 0 publications

Functionalization of Meldrum’s Acid by Diels‒Alder Approach

Functionalization of Meldrum’s Acid by Diels‒Alder Approach

Iodine-DMSO mediated conversion of N-arylcyanothioformamides to N-arylcyanoformamides and the unexpected formation of 2-cyanobenzothiazoles

Synthetic Applications of the Pyrolysis of Meldrum's Acid Derivatives

Contact Info

Product

Resources

About