U.S. flag

An official website of the United States government

Dot gov

Official websites use .gov
A .gov website belongs to an official government organization in the United States.

Https

Secure .gov websites use HTTPS
A lock ( ) or https:// means you’ve safely connected to the .gov website. Share sensitive information only on official, secure websites.

PubAg

Main content area

You searched for: Journal name Journal of organic chemistry Remove constraint Journal name: Journal of organic chemistry Publication year rev 7978-2022 Remove constraint Publication year rev: 7978-2022 Source 2022 v.87 no.5 Remove constraint Source: 2022 v.87 no.5
Start Over

Search

168  Search Results

« Previous | 1 - 20 of 168 |
Number of results to display per page

Search Results

1. 1,3-Asymmetric Induction in Diastereoselective Allylations of Chiral N-Tosyl Imines

Author:
Anna Lo; David A. Gutierrez; Garrett Toth-Williams; James C. Fettinger; Jared T. Shaw
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 2773-2778
ISSN:
1520-6904
Subject:
Lewis acids; aldimines; allylation; diastereoselectivity; organic chemistry
Abstract:
... Lewis acid mediated allylations of β-alkoxy N-tosyl imines using allyltrimethylsilane lead to 3-alkoxy homoallylic N-tosyl amines with anti-selectivity. Two methods of Cu(OTf)₂-mediated allylations are reported herein, demonstrating that diastereoselectivity can be achieved through 1,3 acyclic stereocontrol of β-chiral aldimines. Observed selectivity trends and computational evidence suggest selec ...
DOI:
10.1021/acs.joc.1c02691

2. 3,6,13,16-Tetrapropylporphycene: Rational Synthesis, Complexation, and Halogenation

Author:
Jodukathula Nagamaiah; Arnab Dutta; Narendra Nath Pati; Sameeta Sahoo; Rahul Soman; Pradeepta K. Panda
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 2721-2729
ISSN:
1520-6904
Subject:
divalent metals; fluorescence; organic chemistry; photochemotherapy; singlet oxygen
Abstract:
... We have designed and synthesized 3,6,13,16-tetrapropylporphycene for the first time as its alkyl analogue from ethyl 4-propyl-1H-pyrrole-2-carboxylate. The substituent effect was found to be more intense than reported positional isomeric tetrapropylporphycenes. The freebase porphycene exhibited moderate fluorescence and complexation ability with divalent metal ions, including Zn(II), which display ...
DOI:
10.1021/acs.joc.1c02652

3. 5-Bromo-2-chloro-4-fluoro-3-iodopyridine as a Halogen-rich Intermediate for the Synthesis of Pentasubstituted Pyridines

Author:
Yong-Jin Wu; Gerard J. Porter; David B. Frennesson; Mark G. Saulnier
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 2559-2568
ISSN:
1520-6904
Subject:
Lewis acids; bromine; chlorine; fluorine; iodine; organic chemistry; pyridines
Abstract:
... The 60 individual halopyridine isomers that contain one bromine, chlorine, fluorine, iodine, and H are valuable potential building blocks in medicinal chemistry research, but surprisingly, there has been only one report on the synthesis of just two of them. Herein, we describe simple syntheses of the unique 5-bromo-2-chloro-4-fluoro-3-iodopyridine (10) and 3-bromo-6-chloro-4-fluoro-2-iodopyridine ...
DOI:
10.1021/acs.joc.1c02507

4. A Green Chemistry Approach toward the Stereospecific Synthesis of Densely Functionalized Cyclopropanes via the Solid-State Photodenitrogenation of Crystalline 1-Pyrazolines

Author:
Trevor Y. Chang; Daniel M. Adrion; Alana Rose Meyer; Steven A. Lopez; Miguel A. Garcia-Garibay
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 2277-2288
ISSN:
1520-6904
Subject:
density functional theory; drugs; green chemistry; nanocrystals; organic chemistry; photochemical reactions; positional isomers; regioselectivity; stereospecificity
Abstract:
... The cyclopropane ring features prominently in active pharmaceuticals, and this has spurred the development of synthetic methodologies that effectively incorporate this highly strained motif into such molecules. As such, elegant solutions to prepare densely functionalized cyclopropanes, particularly ones embedded within the core of complex structures, have become increasingly sought-after. Here we ...
DOI:
10.1021/acs.joc.1c01808

5. A Metal-Free Path to 2-Iodo-3-alkyl-1-arylbut-2-en-1-ones and Their Application to the Domino Synthesis of Functionalized 2H-Pyran-2-ones

Author:
Chinnabattigalla Sreenivasulu; Gedu Satyanarayana
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 2222-2240
ISSN:
1520-6904
Subject:
isomerization; organic chemistry; palladium
Abstract:
... We report a metal-free selective synthesis of 2-iodo-3-alkyl-1-arylbut-2-en-1-ones from propargylic alcohols that is enabled by N-iodosuccinimide. A variety of substituted propargylic alcohols are amenable to delivering the selective 2-iodoenone products in very good yields. The utility of the α-iodoenone derivatives is further extended by developing an efficient, novel, and new synthetic methodol ...
DOI:
10.1021/acs.joc.1c03061

6. A Molecular Iodine-Mediated Synthesis of Cyclopenta[c]furo[3,2-b]furan-5,6-diones: Assembly of an Angular Dioxatriquinane Core

Author:
Issa Yavari; Ramin Mohsenzadeh; Parisa Ravaghi
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 2616-2623
ISSN:
1520-6904
Subject:
X-radiation; chemical reactions; organic chemistry; pyridines; stereochemistry
Abstract:
... A molecular iodine-mediated synthesis of angular oxatriqinane core from 3-acetyl-2H-chromen-2-ones, β-bromo-β-nitrostyrenes, and pyridine in the presence of Et₃N in MeCN containing a trace amount of water was developed. The reaction proceeds via intermolecular Michael reaction of 2-oxo-2-(2-oxo-2H-chromen-3-yl)-1-(pyridin-1-ium-1-yl)ethan-1-ide with bromonitrostyrene followed by intramolecular Mic ...
DOI:
10.1021/acs.joc.1c02572

7. Additive-Controlled Divergent Synthesis of Indole and 4H-Benzo[d][1,3]oxazine Derivatives: Palladium-Catalyzed Carbonylative Cyclization of 2-Alkynylanilines and Benzyl Chlorides

Author:
Qi Wang; Lingyun Yao; Jian-Shu Wang; Jun Ying; Xiao-Feng Wu
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 3874-3882
ISSN:
1520-6904
Subject:
additives; indoles; journals; organic chemistry
Abstract:
... A palladium-catalyzed divergent carbonylative synthesis of indoles and 4H-benzo[d][1,3]oxazines from 2-alkynylanilines and benzyl chlorides with benzene-1,3,5-triyl triformate (TFBen) as the CO source has been developed. The reaction using AlCl₃ as the additive produced various indoles in high yields, while a series of 4H-benzo[d][1,3]oxazines was achieved in moderate yields with AcOH as the addit ...
DOI:
10.1021/acs.joc.2c00006

8. An Approach to Modify 14-Membered Lactone Macrolide Antibiotic Scaffolds

Author:
Anna Janas; Krystian Pyta; Maria Gdaniec; Piotr Przybylski
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 3758-3761
ISSN:
1520-6904
Subject:
X-radiation; ketolides; organic chemistry; temperature
Abstract:
... A ketolide derivative with (12R)-configuration was obtained via a novel ketene acetal in acidic conditions. The structure of this atypical β-keto ketene acetal intermediate within the macrocyclic system has been determined by NMR and X-ray methods. The use of basic conditions at an elevated temperature yielded new, doubly α,β-unsaturated ketone macrolide derivatives with (4E)-configuration as two ...
DOI:
10.1021/acs.joc.1c02799

9. Asymmetric Hydrogenation of Racemic Allylic Alcohols via an Isomerization–Dynamic Kinetic Resolution Cascade

Author:
Kun Wang; Saisai Niu; Xin Guo; Weijun Tang; Dong Xue; Jianliang Xiao; Huaming Sun; Chao Wang
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 3804-3809
ISSN:
1520-6904
Subject:
alcohols; hydrogenation; isomerization; organic chemistry
Abstract:
... Prochiral racemic allylic alcohols are converted to enantioenriched chiral alcohols bearing adjacent stereocenters catalyzed by a diamine diphosphine Ru complex in the presence of tBuOK. The protocol features a broad substrate scope (56 examples) and high diastereo- and enantioselectivities (up to >99:1 dr, >99% ee) and could be applied to the synthesis of enantioenriched chromane and indane compo ...
DOI:
10.1021/acs.joc.1c02916

10. Asymmetric Total Synthesis and Structure Elucidation of Huperzine H

Author:
Shinya Shiomi; Kaewsri Wilailak; Wataru Soutome; Hiromitsu Takayama; Mariko Kitajima; Hayato Ishikawa
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 3730-3735
ISSN:
1520-6904
Subject:
Lewis bases; cyclization reactions; diastereoselectivity; organic chemistry; pyrroles; silyl enol ethers; stereochemistry
Abstract:
... A first asymmetric total synthesis of huperzine H has been achieved in a 12% overall yield from commercially available (+)-pulegone. The key steps of this synthesis include a highly diastereoselective Mukaiyama–Michael addition reaction of a pyrrole bearing a silyl enol ether and an intramolecular SN2 cyclization reaction with iodinated pyrrole acting as an effective nucleophile for the formation ...
DOI:
10.1021/acs.joc.1c02672

11. Aza-Oxyallyl Cation Driven 3-Amido Oxetane Rearrangement to 2-Oxazolines: Access to Oxazoline Amide Ethers

Author:
Irshad Maajid Taily; Debarshi Saha; Prabal Banerjee
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 2155-2166
ISSN:
1520-6904
Subject:
Lewis acids; alkylation agents; cations; organic chemistry
Abstract:
... Herein, we report a highly facile and unprecedented activation of 3-amido oxetanes to synthesize 2-oxazoline amide ethers using a transient electrophilic aza-oxyallyl cation as an activating as well as an alkylating agent under mild reaction conditions. The aza-oxyallyl cation driven intramolecular rearrangement of 3-amido oxetanes to 2-oxazolines is the hallmark of this transformation and is a ne ...
DOI:
10.1021/acs.joc.1c03108

12. Bis-(Fluorene)-Embedded Hexaphyrins

Author:
Bharti Yadav; Mangalampalli Ravikanth
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 2543-2550
ISSN:
1520-6904
Subject:
absorption; air; ambient temperature; density functional theory; electrochemistry; energy; fluorenes; mass spectrometry; nuclear magnetic resonance spectroscopy; organic chemistry; oxidation
Abstract:
... The polyaromatic hydrocarbon containing expanded porphyrins, bis-(fluorene)-embedded hexaphyrins, were synthesized by condensing fluorene-based tripyrrane with pentafluorobenzaldehyde in CH₂Cl₂ in the presence of 1 equiv of BF₃·OEt₂ under an inert atmosphere followed by oxidation with DDQ in open air at room temperature. The reaction worked only when 1 equiv of BF₃·OEt₂ was added to the reaction m ...
DOI:
10.1021/acs.joc.1c02488

13. Chemoselective Cleavage of Acylsulfonamides and Sulfonamides by Aluminum Halides

Author:
Dayong Sang; Bingqian Dong; Yunfeng Liu; Juan Tian
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 3586-3595
ISSN:
1520-6904
Subject:
acetonitrile; aluminum; chemoselectivity; iodine; organic chemistry
Abstract:
... The chemoselective cleavage of C–N bonds of amides, sulfonamides, and acylsulfonamides by aluminum halides is described. AlCl₃ and AlI₃ display complementary reactivities toward N-alkyl and N-acyl moieties. N-Alkylacylsulfonamides, secondary N-(tert-butyl)sulfonamides, and tertiary N-(tert-butyl)amides undergo N-dealkylation upon treatments with AlI₃ generated in situ from aluminum and iodine in a ...
DOI:
10.1021/acs.joc.1c03133

14. Copper(I)-Catalyzed Direct Oxidative Annulation of 1,3-Dicarbonyl Compounds with Maleimides: Access to Polysubstituted Dihydrofuran Derivatives

Author:
Wen-Kang Wang; Hong-Ru Tan; Ning-Ning Wang; Hong-Li Ruan; Sheng-Yin Zhao
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 2711-2720
ISSN:
1520-6904
Subject:
copper; organic chemistry; oxidation; pyrroles
Abstract:
... An efficient annulation method for the synthesis of polysubstituted dihydrofurans from 1,3-dicarbonyl compounds and maleimides is described. The reactions can afford furo[2,3-c]pyrrole derivatives with satisfactory yields. The developed strategy realizes the direct oxidative double C(sp³)–H functionalization in the presence of copper(I) salts and 2-(tert-butylperoxy)-2-methylpropane. Meanwhile, th ...
DOI:
10.1021/acs.joc.1c02648

15. Cp*Rh(III)-Catalyzed Regioselective C(sp²)–H Mono- and Dialkynylation of Thioamides by Sulfur Coordination

Author:
Lin Ma; Xiaohui Zhang; Yanyan Tuo; Qing-Zhong Zheng
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 3691-3700
ISSN:
1520-6904
Subject:
drugs; organic chemistry; regioselectivity; sulfur; thioamides
Abstract:
... An efficient Cp*Rh(III)-catalyzed regioselective C(sp²)–H mono- and dialkynylation of thioamides was described. This reaction was performed under mild conditions in high yields (up to 98%) with a broad substrate scope. Significantly, the versatility of this method was further demonstrated by controlled mono- and dialkynylation. Application of this protocol in the late stage functionalization of tw ...
DOI:
10.1021/acs.joc.1c02622

16. Dual Role of Oxoaldehydes: Divergent Synthesis of 3-Aryl- and 3-Aroylcoumarins

Author:
Ali Moazzam; Meysam Khodadadi; Farnaz Jafarpour; Mehdi Ghandi
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 3630-3637
ISSN:
1520-6904
Subject:
arylation; coumarins; cross-coupling reactions; organic chemistry
Abstract:
... A facile and efficient synthetic approach to various valuable 3-aryl- and 3-aroylcoumarins by the direct arylation and aroylation of coumarins with glyoxals in a metal-free manner is presented. The aryl glyoxal is for the first time recognized to serve as an aryl surrogate in addition to its role as an aroyl transfer reagent via a simple switch in reaction conditions. The approach accommodates a b ...
DOI:
10.1021/acs.joc.1c02159

17. Employing Visible-Light Photoredox Catalysis in Multicomponent–Multicatalyst Reactions: One-Pot Synthesis of Spiroquinazolin-2-(thi)ones

Author:
Zhentao Pan; Xuancheng Yang; Bo Chen; Shuaijun Shi; Tong Liu; Xuqiong Xiao; Linlin Shen; Li Lou; Yongmin Ma
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 3596-3604
ISSN:
1520-6904
Subject:
air; catalytic activity; energy; light; organic chemistry; oxidants; redox reactions; solvents; synthesis
Abstract:
... The multicomponent–multicatalyst reaction ((MC)²R) and visible-light catalysis have emerged as green and powerful strategies for achieving ideal syntheses. Here, we report the first example of a visible-light-induced approach toward spiroquinazolin(thi)ones. This (MC)²R features an eco-friendly energy source and solvent, metal-free catalysts, step- and atom-economy, a relay catalysis strategy, air ...
DOI:
10.1021/acs.joc.1c03151

18. Formation of Breslow Intermediates under Aprotic Conditions: A Computational Study

Author:
Gou-Tao Huang; Ming-Hsiu Hsieh; Jen-Shiang K. Yu
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 2501-2507
ISSN:
1520-6904
Subject:
benzaldehyde; density functional theory; hydrogen bonding; organic chemistry; zwitterions
Abstract:
... The mechanism of formation of the Breslow intermediate (BI) under aprotic conditions is investigated with density functional theory (DFT) calculations. The zwitterionic adduct (ZA) is formed by the first addition of an imidazolinylidene to benzaldehyde. The forward reaction is found to proceed through the second addition of the ZA to another benzaldehyde, and subsequent proton migration gives a he ...
DOI:
10.1021/acs.joc.1c02408

19. General Enantioselective and Stereochemically Divergent Four-Stage Approach to Fused Tetracyclic Terpenoid Systems

Author:
Joshua M. Nicholson; Adam B. Millham; Andrea R. Bucknam; Lauren E. Markham; Xenia Ivanna Sailors; Glenn C. Micalizio
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 3352-3362
ISSN:
1520-6904
Subject:
carbon; cardenolides; cross-coupling reactions; enantioselectivity; epichlorohydrins; limonoids; organic chemistry; stereochemistry; therapeutics
Abstract:
... Tetracyclic terpenoid-derived natural products are a broad class of medically relevant agents that include well-known steroid hormones and related structures, as well as more synthetically challenging congeners such as limonoids, cardenolides, lanostanes, and cucurbitanes, among others. These structurally related compound classes present synthetically disparate challenges based, in part, on the po ...
DOI:
10.1021/acs.joc.1c02979

20. Green Tandem [5C + 1C] Cycloaromatization of α-Alkenoyl Ketene Dithioacetals and Nitroethane in Water: Eco-Friendly Synthesis of Ortho-Acylphenols

Author:
Haifeng Yu; Zheyu Zhang; Xue Zhang; Yupeng Xu; Dongyue Huo; Lanyun Zhang; Wenju Wang
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 2985-2996
ISSN:
1520-6904
Subject:
aromatization; exhibitions; journals; organic chemistry; solvents
Abstract:
... For the first time, an eco-friendly and sustainable tandem [5C + 1C] cycloaromatization of α-alkenoyl ketene dithioacetals and nitroethane in water for the efficient synthesis of ortho-acylphenols was reported. In refluxing water, a range of α-alkenoyl ketene dithioacetals and nitroethane smoothly underwent tandem Michael addition/cyclization/aromatization reactions in the presence of 2.0 equivale ...
DOI:
10.1021/acs.joc.1c02825