Rhodium(II)-catalyzed reactions of 3-diazo-2,4-chromenediones. First one-step synthesis of pterophyllin 2

Lee, Yong Rok; Suk, Jung Yup; Kim, Byung So

doi:10.1016/s0040-4039(99)01317-9

Cited by 55 publications

(17 citation statements)

References 35 publications

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“…As shown in Scheme 11, the use of vinyl ethers instead of allyl iodide resulted also in the regioselective formation of compounds 28, thus confirming the generality of this synthetic route to dihydrofuro[3,2-c]coumarins from diazo compounds and activated olefins [78,80]. However, we must note that the reaction of 3-diazo-2,4-chromenedione with vinyl acetate yielded a mixture of the two regioisomeric cycloadducts 29 and 30 (Scheme 12) [78].…”

Section: Furan-ring Constructionmentioning

confidence: 57%

“…Several catalytic systems have been described for this process, with those based on rhodium(II) complexes, and particularly Rh 2 (OAc) 4 , being the most effective catalyst to generate the reactive metal-carbenoid species. In this context, several iodomethyl-substituted dihydrofuro[3,2-c]coumarins 26 were synthesized in a regioselective manner through a formal Rh 2 (OAc) 4 -catalyzed [3 + 2] cycloaddition of different 3-diazo-2,4-chromenediones 25 with allyl iodide (Scheme 11) [78,79]. From them, the corresponding furo[3,2-c]coumarins 27 were obtained in high yields upon treatment with 1,8-diazabicyclo [5.4.0]undec-7-ene [79].…”

Section: Furan-ring Constructionmentioning

confidence: 99%

“…Following this approach, pterophyllin 2 (33), a natural furo[3,2-c]coumarin isolated from the bark of the evergreen tree Ekebergia pterophylla [82], could be obtained in one-step from 3-diazo-5-methyl-2,4-chromenedione and 2-methyl-1-buten-3-yne (Scheme 14) [78]. The linear isomer 34, easily separable by column chromatography, was also formed in the reaction.…”

Section: Furan-ring Constructionmentioning

confidence: 99%

See 2 more Smart Citations

Metal-Catalyzed Routes for the Synthesis of Furocoumarins and Coumestans

Cadierno

2015

Green Synthetic Approaches for Biologically Relevant Heterocycles

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Section: Furan-ring Constructionmentioning

confidence: 57%

Section: Furan-ring Constructionmentioning

confidence: 99%

Section: Furan-ring Constructionmentioning

confidence: 99%

See 1 more Smart Citation

Metal-Catalyzed Routes for the Synthesis of Furocoumarins and Coumestans

Cadierno

2015

Green Synthetic Approaches for Biologically Relevant Heterocycles

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“…Although several methods of synthesis are presently known [ 7 , 8 ], new approaches for the rapid and selective construction of furochromen-2-one scaffolds are still highly desirable. In this context, recent efforts by different groups have been focused in the one-pot synthesis of furo[3,2- c ]chromen-2-ones ( Figure 1 ) from readily available starting materials, with successful examples including CAN-mediated cycloaddition of 4-hydroxychromen-2-one with terminal alkynes [ 9 , 10 ], rhodium(II)-catalyzed heterocyclization of 3-diazo-2,4-chromenediones with terminal alkynes [ 11 , 12 ], cascade addition/cyclization/oxidation of 3-alkynyl-chromones [ 13 , 14 ], Sonogashira-acetylide coupling/demethylation/cyclization of 3-iodo-4-methoxychromen-2-ones [ 15 , 16 ] and alkynylation/hydroalkoxylation of 3-bromo-4-acetoxychromen-2-ones [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Expeditious Entry to Novel 2-Methylene-2,3-dihydrofuro[3,2-c] chromen-2-ones from 6-Chloro-4-hydroxychromen-2-one and Propargylic Alcohols

Nebra

Díaz‐Álvarez

Dı́ez³

et al. 2011

Molecules

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“…Many research groups further investigated the scope of the Rh(II)-catalyzed synthesis of furans from alkynes and a-diazocarbonyl compounds [194,[209][210][211][212][213][214][215][216][217][218][219][220][221]. Some representative results are summarized in Scheme 8.70.…”

mentioning

confidence: 99%

Transition Metal‐Catalyzed Synthesis of Monocyclic Five‐Membered Aromatic Heterocycles

Dudnik

Gevorgyan

2010

Catalyzed Carbon‐Heteroatom Bond Formation

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Aromatic heterocycles, particularly furans and pyrroles, are structural motifs found in a vast number of biologically active natural and artificial compounds [1][2][3]. Other examples of practical applications of furans and pyrroles include dyes, polymers, and electronic materials [4]. Moreover, these heterocycles are employed as important intermediates in organic synthesis [5][6][7][8][9]. The successful application of furans and pyrroles in these and many other ways and their significance in applied and fundamental areas have placed them at the forefront of contemporary organic chemistry. A variety of methodologies and different protocols for their synthesis have been reported [1-3, 10-23] and become well established throughout decades. Among the variety of novel approaches for the synthesis of furans and pyrroles, transition metal-catalyzed transformations are arguably the most attractive methodologies . Several excellent reviews on the transition metal-catalyzed synthesis of monocyclic five-membered heterocycles have been published in the literature. Many of them were categorized by either the metal or the type of transformation. This chapter covers transition metal-catalyzed syntheses of furans and pyrroles. The main organization of this chapter is based on a heterocycle, wherein syntheses of a particular core are structured by the type of transformation and substrates engaged. Herein, we have tried to discuss equally the synthetic applicability of a method and mechanistic aspects and concepts implicated in the described transformations. A discussion of the mechanisms is given when needed to provide an idea about possible reaction pathways and the nature of the elementary processes involved in the catalytic transformation. It should be noted that the most essential and general catalytic reactions, as well as recent and conceptionally interesting transformations, are discussed in more detail in this chapter. Syntheses of furans and pyrroles via functionalization of the preexisting heterocyclic cores [37,[52][53][54][55][56][57][58][59][60] are not covered and, therefore, only reactions in which assembly of a heterocyclic ring occurs are described. In addition, the Pd-catalyzed synthesis of heterocycles is not covered herein, as this topic is covered in Chapter 6.

show abstract

Rhodium(II)-catalyzed reactions of 3-diazo-2,4-chromenediones. First one-step synthesis of pterophyllin 2

Cited by 55 publications

References 35 publications

Metal-Catalyzed Routes for the Synthesis of Furocoumarins and Coumestans

Metal-Catalyzed Routes for the Synthesis of Furocoumarins and Coumestans

Expeditious Entry to Novel 2-Methylene-2,3-dihydrofuro[3,2-c] chromen-2-ones from 6-Chloro-4-hydroxychromen-2-one and Propargylic Alcohols

Transition Metal‐Catalyzed Synthesis of Monocyclic Five‐Membered Aromatic Heterocycles

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