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1.
J Org Chem ; 87(2): 1262-1271, 2022 Jan 21.
Article in English | MEDLINE | ID: mdl-34989227

ABSTRACT

There are some synthesis methods from widely available aldehydes to the corresponding ketones, however, they involved in multistep reactions with Grignard's reagents or transition metal catalysts. In this paper, we have developed photocatalyst-free and visible light-driven decarboxylative alkylation of pyridinaldehydes. The photochemical reactions are initiated via photoinduced single electron transfer from triethylamine to N-hydroxyphthalimide esters in electron donor-acceptor complexes. This photochemical method can achieve to translate 15 pyridinaldehydes and 11 2-quinolinaldehydes to the corresponding ketones. Furthermore, this strategy can also achieve two other transformations, disulfanes to aryl sulfides and a styrene sulfone to the alkyl-substituted alkene.

2.
J Org Chem ; 86(17): 12419-12426, 2021 Sep 03.
Article in English | MEDLINE | ID: mdl-34379421

ABSTRACT

A metal-free, photocatalyst-free, photochemical system was developed for the direct alkylation of thiophenols via electron donor-acceptor (EDA) complexes (KEDA = 145 M-1) between two reactants, N-hydroxyphthalimide esters as acceptors and thiophenol anions as donors, in the presence of a tertiary amine. The EDA complexes in the reaction system have a broad range of visible-light absorption (400-650 nm) and can trigger the reaction effectively under sunlight.

3.
J Org Chem ; 86(12): 8308-8318, 2021 Jun 18.
Article in English | MEDLINE | ID: mdl-34042446

ABSTRACT

A facile and effective synthesis of 2-chloromethylpyridines was developed by a one-pot reaction of 2-alkylpyridin-N-oxides and triphosgene at room temperature. As starting materials, N-oxides of 2-alkylpyridine derivatives, including 2-alkylpyridines, 2-methyl quinolines, and phenanthroline, can react rapidly with triphosgene in the presence of triethylamine, affording 2-chloromethylpyridines in good to excellent yields (52-95%). Using the 2-methylquinoline substrate for the mechanistic study, it has been well demonstrated that the chlorination reaction undergoes a [3,3]-sigmatropic rearrangement, which can be observed as a reversible process by monitoring the intermediates. Moreover, the chlorination reaction can be used to construct a rapid and sensitive fluorescent probe for the detection of phosgene.

4.
Virology ; 531: 162-170, 2019 05.
Article in English | MEDLINE | ID: mdl-30884426

ABSTRACT

Limited sampling means that relatively little is known about the diversity and evolutionary history of mammalian members of the Hepadnaviridae (genus Orthohepadnavirus). An important case in point are shrews, the fourth largest group of mammals, but for which there is limited knowledge on the role they play in viral evolution and emergence. Here, we report the discovery of a novel shrew hepadnavirus. The newly discovered virus, denoted shrew hepatitis B virus (SHBV), is divergent to be considered a new species of Orthohepadnavirus. Phylogenetic analysis revealed that these viruses were usually most closely related to TBHBV (tent-making bat hepatitis B virus), known to be able to infect human hepatocytes, and had a similar genome structure, although SHBV fell in a more basal position in the surface protein phylogeny. In sum, these data suggest that shrews are natural hosts for hepadnaviruses and may have played an important role in their long-term evolution.


Subject(s)
Evolution, Molecular , Hepadnaviridae Infections/veterinary , Hepadnaviridae Infections/virology , Hepadnaviridae/isolation & purification , Shrews/virology , Amino Acid Sequence , Animals , China , Genome, Viral , Hepadnaviridae/chemistry , Hepadnaviridae/classification , Hepadnaviridae/genetics , Hepadnaviridae Infections/transmission , Hepatocytes/virology , Humans , Orthohepadnavirus/classification , Orthohepadnavirus/genetics , Orthohepadnavirus/isolation & purification , Phylogeny , Sequence Alignment , Shrews/classification , Viral Proteins/chemistry , Viral Proteins/genetics
5.
Virology ; 514: 88-97, 2018 01 15.
Article in English | MEDLINE | ID: mdl-29153861

ABSTRACT

To better understand the evolution of hepadnaviruses, we sampled bats from Guizhou, Henan and Zhejiang provinces, China, and rodents from Zhejiang province. Genetically diverse hepadnaviruses were identified in a broad range of bat species, with an overall prevalence of 13.3%. In contrast, no rodent hepadnaviruses were identified. The newly discovered bat hepadnaviruses fell into two distinct phylogenetic groups. The viruses within the first group exhibited high diversity, with some closely related to viruses previously identified in Yunnan province. Strikingly, the newly discovered viruses sampled from Jiyuan city in the second phylogenetic group were most closely related to those found in bats from West Africa, suggestive of a long-term association between bats and hepadnaviruses. A co-phylogenetic analysis revealed frequent cross-species transmission among bats from different species, genera, and families. Overall, these data suggest that there are likely few barriers to the cross-species transmission of bat hepadnaviruses.


Subject(s)
Chiroptera/virology , Evolution, Molecular , Genetic Variation , Hepadnaviridae Infections/veterinary , Hepadnaviridae/genetics , Hepadnaviridae/isolation & purification , Animals , China , Genome, Viral , Hepadnaviridae/classification , Hepadnaviridae Infections/virology , Phylogeny
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