Metal‐Free Electrochemical [3+2] Cycloaddition between α‐Amino Carbonyls and Tosylmethyl Isocyanide en route to Substituted Imidazoles DOI

Samrat Mallick,

Mrinmay Baidya, Suman De Sarkar

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 366(2), С. 241 - 247

Опубликована: Ноя. 24, 2023

Abstract The established strategy unveils a metal and mediator‐free electrochemical [3+2] cycloaddition approach among α ‐amino carbonyls tosylmethyl isocyanide (TosMIC) fabricating substituted imidazole scaffolds. Implementation of electro‐redox conditions on this eliminates the essential requirement transition catalysts chemical oxidants. A wide variety different functionalities are well tolerated under reaction condition, contributing to substrate scope applicability. Several control experiments cyclic voltammetry studies suggest an electro‐oxidation triggered successive C−C C−N bond formations followed by rapid aromatization for constructing five‐membered core structure.

Язык: Английский

Enantiodivergent Synthesis of (+)- and (–)-Crispine A DOI
Yu Wang,

Zuming Lin,

Sha‐Hua Huang

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(3), С. 1021 - 1021

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

1

Base-Mediated Cascade Lactonization/1,3-Dipolar Cycloaddition Pathway for the One-Pot Assembly of Coumarin-Functionalized Pyrrolo[2,1-a]isoquinolines DOI
Qiang Tang, Yanan Liu,

Binbin Fei

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8420 - 8434

Опубликована: Июнь 5, 2024

An elegant and highly concise strategy for the construction of coumarin-functionalized pyrrolo[2,1-a]isoquinolines from available propargylamines isoquinolinium N-ylides has been disclosed. In this reaction, acted as a C2 synthon to form coumarin ring well 1,3-dipole construct pyrrole in single pot. This cascade process involves 1,4-conjugate addition/lactonization/1,3-dipolar cycloaddition four chemical bonds (one C–O bond three C–C bonds) two new heterocyclic skeletons. Additionally, most these compounds showed good fluorescence properties exhibited high molar extinction coefficient large Stokes shifts.

Язык: Английский

Процитировано

7

Nitration of Pyrrolo[2,1-a]isoquinolines DOI

Xiao‐Hui Chen,

Dandan Ma,

Xin Gao

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(7), С. 4649 - 4661

Опубликована: Март 22, 2023

We have successfully modified a series of pyrrolo[2,1-a]isoquinolines via direct nitration under mild reaction conditions. Easily accessible nitrates including CAN, Cu(NO3)2·H2O, and Fe(NO3)3·9H2O all can serve as effective nitrating reagents for functionalizing pyrrolo[2,1-a]isoquinolines. Various nitro-bearing been efficiently prepared in acceptable to good yields.

Язык: Английский

Процитировано

14

Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines through Decarboxylative/Dehydrofluorinative [3 + 2] Cycloaddition Aromatization of Isoquinolinium N-Ylides with Difluoroenoxysilanes DOI

Wenxue Xi,

Yiheng Zhang, Haijian Wu

и другие.

Organic Letters, Год журнала: 2023, Номер 25(26), С. 4908 - 4912

Опубликована: Июнь 23, 2023

A decarboxylative/dehydrofluorinative formal [3 + 2] cycloaddition aromatization of isoquinolinium N-ylides with difluoroenoxysilanes has been developed. This methodology provides a facile and straightforward synthetic pathway to afford highly functionalized fluorinated pyrrolo[2,1-a]isoquinolines in good excellent yields under mild conditions. Moreover, gram-scale derivatization experiments for the late-stage functionalization drug molecules have also demonstrated.

Язык: Английский

Процитировано

13

An Overview on the Synthesis of Lamellarins and Related Compounds with Biological Interest DOI Creative Commons

Vasiliki-Panagiota M. Mitsiou,

Anastasia-Maria N. Antonaki,

Matina D. Douka

и другие.

Molecules, Год журнала: 2024, Номер 29(17), С. 4032 - 4032

Опубликована: Авг. 26, 2024

Lamellarins are natural products with a [3,4]-fused pyrrolocoumarin skeleton possessing interesting biological properties. More than 70 members have been isolated from diverse marine organisms, such as sponges, ascidians, mollusks, and tunicates. There is continuous interest in the synthesis of these compounds. In this review, synthetic strategies for title compounds presented along their Three routes followed lamellarins. Initially, pyrrole derivatives starting or intermediate compounds, then they fused to isoquinoline coumarin moiety. Second, compound an indole last route, coumarins which moiety scaffold. The isolamellarins, azacoumestans, isoazacoumestans, analogues also described. above achieved via metal-catalyzed cross-coupling, [3 + 2] cycloaddition, substitution, lactonization reactions. exhibit cytotoxic, multidrug resistance (MDR), topoisomerase I-targeted antitumor, anti-HIV, antiproliferative, anti-neurodegenerative disease, anti-inflammatory activities.

Язык: Английский

Процитировано

5

Bromination of Pyrrolo[2,1-a]isoquinolines with Acetyl Bromide and Dimethyl Sulfoxide DOI
Hai‐Lei Cui

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(5), С. 2822 - 2831

Опубликована: Фев. 10, 2023

A mild bromination of pyrrolo[2,1-a]isoquinolines has been achieved using acetyl bromide and dimethyl sulfoxide. series brominated could be obtained in moderate to excellent yields (46-99%) at room temperature. This strategy can also expanded the facile polysubstituted pyrroles, indoles, electron-rich phenols, aniline, 2-naphthol.

Язык: Английский

Процитировано

10

Synthesis of mono-fluorinated heterocycles with a ring-junction nitrogen atom via Rh(iii)-catalyzed CF3-carbenoid C–H functionalization and defluorinative annulation DOI
Haosheng Li,

Mingjing Mei,

Duo‐Zhi Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(6), С. 1544 - 1550

Опубликована: Янв. 1, 2023

A Rh-catalyzed two-fold C–F bond cleavage enabled [4 + 2] annulation reaction via CF 3 -carbenoid C–H functionalization of arenes with indoles or various classes azoles as the directing groups was developed.

Язык: Английский

Процитировано

10

Organocatalytic regio- and enantioselective C1-arylation of β,γ-alkynyl-α-imino esters with pyrrolo[2,1-a]isoquinolines DOI
Xuan Zhang, Xiaoxiao Song, Qijian Ni

и другие.

Chemical Communications, Год журнала: 2023, Номер 60(7), С. 831 - 834

Опубликована: Дек. 15, 2023

We herein report regio- and enantioselective arylation of β,γ-alkynyl-α-imino esters with pyrroloisoquinolines. Using chiral phosphoric acid catalysts, a wide range novel axially tetrasubstituted α-amino allenoates were accessed in good yields excellent enantioselectivities. Notably, this transformation occurred preferentially at the sterically more hindered C1-position The potential scalability late-stage functionalization demonstrated utility current protocol.

Язык: Английский

Процитировано

9

One-pot C–N/C–C bond formation and oxidation of donor–acceptor cyclopropanes with tetrahydroisoquinolines: access to benzo-fused indolizines DOI
Pallab Karjee, Bijoy Debnath, Santu Mandal

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(30), С. 4068 - 4071

Опубликована: Янв. 1, 2024

A two step one-pot annulation of donor–acceptor cyclopropanes with tetrahydroisoquinolines has been accomplished to furnish benzo-fused indolizines substrate scope and functional group diversity.

Язык: Английский

Процитировано

3

Modular Assembly of Pyrrolo[3,4-c]isoquinolines through Rh-Catalyzed Cascade C–H Activation/Annulation of O-Methyl Aryloximes with Maleimides DOI

Yinsong Wu,

Yanan Liu,

Yangzilin Kong

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8447 - 8457

Опубликована: Июнь 4, 2024

An efficient and practical strategy for the construction of pyrrolo[3,4-

Язык: Английский

Процитировано

3