2H-Pyran-2-one

B. 2H-Pyran-2-one. A mixture of 9.81 g. (0.100 mole) of 5,6-dihydro-2/I-pyran-2-one, 200 mg. of benzoyl peroxide, 18.6 g. (0.105 mole) of A-bromosuccinimide [2,5-Pyrrolidinedione, 1-bromo-] (Note 7), and 800 ml. of carbon tetrachloride is prepared in a 2-1., three-necked, round-bottomed flask equipped with a reflux condenser and a mechanical stirrer. The resulting suspension is stirred and heated to reflux. After 1.5 hours at reflux, most of the solid is dissolved, and the solution gives a negative test with starch-iodide paper. The reaction mixture is then allowed to cool, dining which time succinimide [2,5-Pyrrolidine-dione] crystallizes out. The precipitate is removed by filtration, and the filtrate is concentrated under reduced pressure to leave crude 5-bromo-5,6 -dihy dro 211 -pyran-2 one [ 211 Py ran - 2-one, 5-bromo-5,6-dihydro] as an oil. 

Propionic acid, 2-iodo-3-nitro-, ethyl ester [Propanoic acid, 2-iodo-3-mtro-, ethyl ester], 65 2//-Pyran, 3,4-dihydro-, 51 2//-PYR AN-2-ONE, 49 2H Pyran 2-one, 5 bromo 5,6-dihydro, 50 27/-PYRAN-2-ONE, 5,6 DIHYDRO-, 49 PYRIDINE, 2,3,4,5 TETRAHYDRO, 118 Pyridines, -substituted, 34 a Pyrone-6-carboxyhc acid [2H Pyran-6-Larboxyhc acid 2-oxo ], 51 Pyrroles, 34... 

A broad study on the MW-assisted Diels Alder reactions of 2H-pyran-2-ones 50 and 51 with 1,4-naphthoquinone 52 and N-phenylmaleimide 53 (Equations 4.3) supported on silica-gel, K-10 montmorillonite, fitrol and alumina was carried out by Samant and colleagues [41]. 

The Diels-Alder reaction of 2H-pyran-2-ones part IV - Microwave catalyzed Diels-Alder reaction of 4,6-disubstituted-2H-pyran-2-ones with 1,4-naphthoquinone and N-phenylmaleimide [41a]... 

Kvita V. and Fischer W. 6-Unsubstituier te 2H-Pyran-2-One-Synthese und Reak-tivitat Chimia 1993 47 33-18 (in German)... 

On reaction of 2H-pyran-2-ones 738 with HMDS 2 and catalytic amounts of DBU, pyridine derivatives 741 are obtained via 739 and 740 in yields of 40-97% [223] (Scheme 5.78). 

Dihydro-2H-pyran-2-ones (e. g., 4-195) are valuable intermediates in the synthesis of several natural products [67]. Hattori, Miyano and coworkers [68] have recently shown that these compounds can be easily obtained in high yield by a Pd2+-catalyzed [2+2] cycloaddition of ct, 3-unsaturated aldehydes 4-192 with ketene 4-193, followed by an allylic rearrangement of the intermediate 4-194 (Scheme 4.42). In this reaction the Pd2+-compound acts as a mild Lewis acid. a,(3-unsaturated ketones can also be used, but the yields are below 20%. 

Synthesis of ( )-trans-6-[4,4-bis(4-fluorophenyl)-3-(1 -methyl- 1H-tetrazol-5-yl)-1 (E), 3-[2- uC]butadienyl-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one... 

The rhodium-catalyzed asymmetric conjugate addition is applicable to a,yS-unsaturated esters (Scheme 3.8). Hayashi reported [20] that the reachon of 5,6-dihydro-2H-pyran-2-one 19a with phenylboronic acid gave a 94% yield of phenylated lactone (S)-20am with 98% enanhomeric excess. For the linear enoates, organoboronic acids did not give... 

An antibiotic inhibition zone often appears around Trichoderma spp. interacting with other fungi. The genus contains many species which produce secondary metabolites. Claydon et al. (23) have identified an antibiotic from T. harzianum as a volatile, 6-n-pentyl-2H-pyran-2-one this was recently shown to be an active antibiotic from T. koningii (24). The volatile appeared to be the factor responsible for the coconut smell of some biocontrol-effective strains of T. harzianum (25). However, in a Petri-plate assay, it can be difficult to be certain that antibiosis is involved. As well as competitive growth, lytic enzymes could also contribute to the action and Trichoderma has been shown to produce / -l,3-glucanase and chitinase (26-29). 

H-Pyran-2-one, 3-acetyl-4-hydroxy-6-methyl-dipole moment, 3, 626 <37JCS1088>... 

N1 - 2H-PYRAN-2-ONE, 5,6-0IHYDR0-4-METH0XY-6-STYRYL-, (R)-, mixt. with 5,6-DIHYDR0-4-METH0XY- 6-PHENETHYL-2H-PYRAN-2-ONE and... 

Carlson, R. M. Oyler, A. R. Peterson, J. R. Synthesis of substituted 5,6-dihydro-2H-pyran-2-ones. Propiolic acid dianion as a reactive three-carbon nucleophile. J. Org. Chem. 1975, 40, 1610-1616. 

So far, most microorganisms and enzymes derived therefrom have been used in the reduction of a single keto group of p-keto or a-keto compounds [68-71], Recently, Patel et al. [72] have demonstrated the stereoselective reduction of 3,5-dioxo-6-(benzyloxy)hexanoic acid, ethyl ester (41), to (3,S, 5R)-dihydroxy-6-(benzyloxy)hexanoic acid, ethyl ester (42a) (Fig. 14). The compound (42a) is a key chiral intermediate required for the chemical synthesis of [4-[4a,6P(E)]]-6-[4,4-bis(4-fluorophenyl)-3-(l-methyl-lH-tetrazol-5-yl)-l,3-butadienyl]-tetrahydro-4-hydroxy-2H-pyran-2-one, compound R-( + )-(43), a new anticholesterol drug that acts by inhibition of HMG CoA reductase [73], Among various microbial cultures evaluated for the stereoselective reduction of diketone (41), cell suspensions of Aci-... 

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