scholarly journals Direct Boronation of Allyl Alcohols with Diboronic Acid Using Palladium Pincer-Complex Catalysis. A Remarkably Facile Allylic Displacement of the Hydroxy Group under Mild Reaction Conditions.

ChemInform ◽  
2006 ◽  
Vol 37 (33) ◽  
Author(s):  
Vilhelm J. Olsson ◽  
Sara Sebelius ◽  
Nicklas Selander ◽  
Kalman J. Szabo
Keyword(s):  
Hydroxy Group ◽  
Reaction Conditions ◽  
Pincer Complex ◽  
Allyl Alcohols

Spontaneous butenolide ring formation of pregnane-21-O-malonyl hemiesters under mild reaction conditions is facilitated by the 14β-hydroxy group present in all natural cardenolides

Tetrahedron ◽  
2016 ◽  
Vol 72 (30) ◽  
pp. 4556-4563 ◽  
Author(s):  
R.M. Pádua ◽  
N. Meitinger ◽  
M. Hennemann ◽  
P. Schebitz ◽  
R. Waibel ◽  
...  
Keyword(s):  
Hydroxy Group ◽  
Ring Formation ◽  
Reaction Conditions

scholarly journals An efficient approach for the synthesis of novel methyl sulfones in acetic acid medium and evaluation of antimicrobial activity

2020 ◽  
Vol 44 (5) ◽  
pp. 1386-1394
Author(s):  
Gollapudi RAVI KUMAR ◽  
Chandra Rao DASIREDDY ◽  
Ravi VARALA ◽  
Vijay KOTRA ◽  
Hari Babu BOLLIKOLLA
Keyword(s):  
Antimicrobial Activity ◽  
Acetic Acid ◽  
Acid Medium ◽  
Room Temperature ◽  
Fungal Infections ◽  
Reaction Conditions ◽  
Acetic Acid Medium ◽  
Mass Spectral ◽  
Allyl Alcohols ◽  
Near Future

A series of nine methyl sulphones (3a–3i) starting from the aldehydes (1a–1i) were synthesized in two consecutive steps. In the first step, preparation of allyl alcohols (2a–2i) from their corresponding aldehydes by the reaction of sodium borohydride in methanol at room temperature is reported. Finally, methyl sulphones are synthesized by condensing sodium methyl sulfinates with allyl alcohols in the presence of BF3.Et2O in acetic acid medium at room temperature for about 2–3 h. The reaction conditions are simple, yields are high (85%–95%), and the products were obtained with good purity. All the synthesized compounds were characterized by their 1H, 13C NMR, and mass spectral analysis. All the title compounds were screened for antimicrobial activity. Among the compounds tested, the compound 3f has inhibited both Gram positive and Gram negative bacteria effectively and compound 3i has shown potent antifungal activity. These promising components may help to develop more potent drugs in the near future for the treatment of bacterial and fungal infections.

Transformation of 8-[(2-Hydroxyalkyl)sulfanyl]adenines to 6-Amino-7H-purin-8(9H)-one Derivatives

2001 ◽  
Vol 66 (9) ◽  
pp. 1393-1406 ◽  
Author(s):  
Zlatko Janeba ◽  
Antonín Holý ◽  
Milena Masojídková
Keyword(s):  
Hydroxy Group ◽  
Alkyl Derivative ◽  
Reaction Conditions ◽  
Derivatives Of ◽  
Adenine Derivative

Alkylation of 6-amino-7H-purin-8(9H)-thione (8-sulfanyladenine, 1) with one equivalent of (R)-[(trityloxy)methyl]oxirane gave its S-alkyl derivative 2, which was converted to the 6-amino-7H-purin-8(9H)-one (3), while alkylation of 1 with two equivalents of (S)-[(trityloxy)methyl]oxirane afforded a mixture of N3,S-dialkylated product 4a, N9-monoalkyl and N7,N9-dialkyl derivatives of 6-amino-7H-purin-8(9H)-one, 5a and 6a, respectively. This approach can be used for rapid and easy transformation of 8-[(2-hydroxyalkyl)sulfanyl]adenines to the derivatives of 6-amino-7H-purin-8(9H)-one (8-hydroxyadenine) using NaH or Cs2CO3 in DMF. The course of the S→O transformation strictly depends on the character of the starting compounds and on the reaction conditions. N9-Alkyl-8-[(2-hydroxyalkyl)sulfanyl]adenines 10, 12, 14 and 17 were rapidly converted to the corresponding 6-amino-7H-purin-8(9H)-one derivatives 11, 13, 11 and 18, respectively. N9-Unsubstituted 2 reacts slowly, and N3-alkyl derivative 4a is stable under the same reaction conditions. The described transformation does not occur when the hydroxy group in 8-[(2-hydroxyalkyl)sulfanyl]adenine derivative 15 is protected. The reaction using NaH proceeds more rapidly than that using Cs2CO3.

scholarly journals Cyclization into Hydrindanes Using Samarium Diiodide: Stereochemical Features Depending on the Protecting Group

2016 ◽  
Vol 11 (8) ◽  
pp. 1934578X1601100
Author(s):  
Masakazu Sono ◽  
Yukiko Nishibuchi ◽  
Norihito Yamaguchi ◽  
Motoo Tori
Keyword(s):  
Hydroxy Group ◽  
Samarium Diiodide ◽  
Protecting Group ◽  
Reaction Conditions ◽  
Bicyclic Compounds

Monocyclic compounds bearing ketone and enone moieties in the same molecule can be cyclized to bicyclic compounds initiated by samarium diiodide. The stereochemistry of the products depended on the reaction conditions and also the protecting group of the hydroxy group existed in the molecule. A cyclization mechanism is discussed.

scholarly journals Electrochemical oxidation of cholesterol

2015 ◽  
Vol 11 ◽  
pp. 392-402 ◽  
Author(s):  
Jacek W Morzycki ◽  
Andrzej Sobkowiak
Keyword(s):  
Double Bond ◽  
Electrochemical Oxidation ◽  
Hydroxy Group ◽  
Electrophilic Addition ◽  
Side Chain ◽  
Reaction Conditions

Indirect cholesterol electrochemical oxidation in the presence of various mediators leads to electrophilic addition to the double bond, oxidation at the allylic position, oxidation of the hydroxy group, or functionalization of the side chain. Recent studies have proven that direct electrochemical oxidation of cholesterol is also possible and affords different products depending on the reaction conditions.

Bu4NI-Catalyzed C–C Bond Cleavage and Oxidative Esterification of Allyl Alcohols with Toluene Derivatives

Synthesis ◽  
2019 ◽  
Vol 51 (19) ◽  
pp. 3667-3674
Author(s):  
Yaoyao Chen ◽  
Chengliang Li ◽  
Yongmei Cui ◽  
Mingming Sun ◽  
Xueshun Jia ◽  
...  
Keyword(s):  
Allyl Alcohol ◽  
Bond Cleavage ◽  
Reaction Conditions ◽  
Oxidative Functionalization ◽  
Oxidative Esterification ◽  
Metal Free ◽  
Bond Forming ◽  
Tetrabutylammonium Iodide ◽  
Allyl Alcohols

A novel oxidative esterification of 1-arylprop-2-en-1-ols with toluene derivatives catalyzed by tetrabutylammonium iodide (TBAI) is reported. The optimization of the reaction conditions illustrates that each of experiment parameters including the catalyst, solvent, and oxidant is significant for present oxidative functionalization. This metal-free protocol has a broad substrate scope including the halogen groups for further functionalization and enriches the reactivity profile of allyl alcohol and toluene derivatives. In addition, this protocol represents a new transformation of allyl alcohol involving C–C bond cleavage and C–O bond forming.

scholarly journals Empowering alcohols as carbonyl surrogates for Grignard-type reactions

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Chen-Chen Li ◽  
Haining Wang ◽  
Malcolm M. Sim ◽  
Zihang Qiu ◽  
Zhang-Pei Chen ◽  
...  
Keyword(s):  
Functional Group ◽  
Early Stage ◽  
Grignard Reaction ◽  
Synthetic Chemistry ◽  
Reaction Conditions ◽  
Type Reaction ◽  
Pincer Complex ◽  
Late Stages

AbstractThe Grignard reaction is a fundamental tool for constructing C-C bonds. Although it is widely used in synthetic chemistry, it is normally applied in early stage functionalizations owing to poor functional group tolerance and less availability of carbonyls at late stages of molecular modifications. Herein, we report a Grignard-type reaction with alcohols as carbonyl surrogates by using a ruthenium(II) PNP-pincer complex as catalyst. This transformation proceeds via a carbonyl intermediate generated in situ from the dehydrogenation of alcohols, which is followed by a Grignard-type reaction with a hydrazone carbanion to form a C-C bond. The reaction conditions are mild and can tolerate a broad range of substrates. Moreover, no oxidant is involved during the entire transformation, with only H2 and N2 being generated as byproducts. This reaction opens up a new avenue for Grignard-type reactions by enabling the use of naturally abundant alcohols as starting materials without the need for pre-synthesizing carbonyls.

Undecagold labeling of tRNA

1991 ◽  
Vol 49 ◽  
pp. 44-45
Author(s):  
James F. Hainfeld ◽  
Kyra M. Alford ◽  
Mathias Sprinzl ◽  
Valsan Mandiyan ◽  
Santa J. Tumminia ◽  
...  
Keyword(s):  
High Resolution ◽  
Transmission Electron Micrograph ◽  
Anticodon Loop ◽  
Electron Micrograph ◽  
Reaction Conditions ◽  
Scanning Transmission Electron ◽  
Transmission Electron ◽  
Scanning Transmission

The undecagold (Au11) cluster was used to covalently label tRNA molecules at two specific ribonucleotides, one at position 75, and one at position 32 near the anticodon loop. Two different Au11 derivatives were used, one with a monomaleimide and one with a monoiodacetamide to effect efficient reactions.The first tRNA labeled was yeast tRNAphe which had a 2-thiocytidine (s2C) enzymatically introduced at position 75. This was found to react with the iodoacetamide-Aun derivative (Fig. 1) but not the maleimide-Aun (Fig. 2). Reaction conditions were 37° for 16 hours. Addition of dimethylformamide (DMF) up to 70% made no improvement in the labeling yield. A high resolution scanning transmission electron micrograph (STEM) taken using the darkfield elastically scattered electrons is shown in Fig. 3.

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