Rh(III)-catalyzed [5+1] spirocyclization to produce novel benzimidazole-incorporated spirosuccinimides DOI Creative Commons

Wei-Yi Pu,

Xinyi Chen, Lin Dong

и другие.

Green Synthesis and Catalysis, Год журнала: 2022, Номер 4(4), С. 338 - 341

Опубликована: Сен. 29, 2022

Transition-metal-catalyzed cross-coupling reactions as very efficient and atom-economical approaches have been widely used to build up complex heterocyclic compounds. However, modification of 2-oxyl benzimidazole skeleton using maleimide compounds via C–H activation has remained unprecedented. Herein, we developed a rhodium(III)-catalyzed [5 ​+ ​1] cascade spiroannulation construct diversified novel benzimidazole-incorporated spirosuccinimide derivatives from benzimidazoles maleimides.

Язык: Английский

Ir(III)-Catalyzed Dual C–H Activation of 2-Aryl Phthalazinediones and 3-Aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides for the Construction of Spiro-Fused Cyclic Frameworks DOI

Devulapally Yogananda Chary,

Minpoor Soumya Reddy,

Chidrawar Ajay

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(5), С. 2758 - 2772

Опубликована: Фев. 21, 2023

An Ir(III)-catalyzed double C–H activation strategy has been developed for the synthesis of highly rigid spiro frameworks by means ortho-functionalization 2-aryl phthalazinediones and 2,3-diphenylcycloprop-2-en-1-ones using Ir(III)/AgSbF6 catalytic system. Similarly, 3-aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides undergo smooth cyclization with to afford a diverse range compounds in good yields excellent selectivity. Additionally, 2-arylindazoles provide corresponding chalcone derivatives under similar reaction conditions.

Язык: Английский

Процитировано

13

Rh(III)-Catalyzed Switchable [4 + 1] and [4 + 2] Annulation of N-Aryl Pyrazolones with Maleimides: An Access to Spiro Pyrazolo[1,2-a]indazole-pyrrolidine and Fused Pyrazolopyrrolo Cinnolines DOI
Chih‐Yu Lin,

Wan‐Wen Huang,

Ying‐Ti Huang

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(6), С. 3424 - 3435

Опубликована: Март 3, 2023

A rhodium(III)-catalyzed controllable [4 + 1] and 2] annulation of N-aryl pyrazolones with maleimides as C1 C2 synthon has been explored for the synthesis spiro[pyrazolo[1,2-a]indazole-pyrrolidines] fused pyrazolopyrrolo cinnolines. The product selectivity was achieved through time-dependent annulation. reaction involves sequential Rh(III)-catalyzed C-H alkenylation pyrazolone, followed by an intramolecular spirocyclization via aza-Michael-type addition to afford spiro[pyrazolo[1,2-a]indazole-pyrrolidine]. However, prolonged time converts in situ formed spiro[pyrazolo[1,2-a]indazole-pyrrolidine] into pyrazolopyrrolocinnoline. This unique formation switch proceeds strain-driven ring expansion a 1,2-shift C-C bond.

Язык: Английский

Процитировано

12

Rh(III)‐Catalyzed C−H Activation/O‐Annulation for Construction of Divergent Spirosuccinimide and Maleimide‐Fused Isochromenes DOI
Eswaran Kamaraj,

Prasanta Roy,

Yong Rok Lee

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(22), С. 3915 - 3926

Опубликована: Сен. 12, 2023

Abstract A rhodium‐catalyzed [5+1] cycloaddition via C−H activation/ O ‐annulation strategy for synthesizing biologically interesting isochromenes is presented. This protocol selectively provides divergently functionalized containing spirosuccinimide and maleimide scaffolds according to the maleimides itaconimides used as substrates. methodology exhibits an extensive substrate scope, remarkable functional group tolerance, high regioselectivity.

Язык: Английский

Процитировано

7

Ruthenium-catalyzed (spiro)annulation of N-aryl-2,3-dihydrophthalazine-1,4-diones with quinones to access pentacyclic spiro-indazolones and fused-cinnolines DOI

Sushma Naharwal,

Pidiyara Karishma,

Chikkagundagal K. Mahesha

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(23), С. 4753 - 4764

Опубликована: Янв. 1, 2022

Ru(II)-catalyzed strategies were developed for the [4 + 1] and 2] oxidative coupling between N-aryl-2,3-dihydrophthalazine-1,4-diones 1,4-benzoquinones, achieving spiro-indazolones fused-cinnolines, respectively. Mild, aerobic external oxidant-free conditions, as well use of a ruthenium catalyst such (spiro)annulative with quinones over reported Rh/Ir-catalyts, underline rewards disclosed protocols.

Язык: Английский

Процитировано

11

Rhodium(iii)-catalysed redox neutral alkylation of 3-arylbenzo[d]isoxazoles: easy access to substituted succinimides DOI

Xuelin Yue,

Xiang Zhao,

Junwei Huang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(29), С. 5985 - 5989

Опубликована: Янв. 1, 2023

A convenient method for the alkylation of 3-arylbenzo[d]isoxazoles with maleimides under redox-neutral conditions has been developed, giving a series substituted succinimides in up to 99% yield. This transformation is highly selective give succinimides, and Heck-type products are successfully avoided. protocol features 100% atom-economy broad substrate tolerance, provides novel strategy synthesis diverse an opportunity succinylation protein medication pharmacologists discover first-in-class drugs.

Язык: Английский

Процитировано

6

Rhodium‐Catalyzed Functionalization and Annulation of N‐Aryl phthalazinediones with Allyl Alcohols DOI

Sushma Naharwal,

Narendra Dinkar Kharat,

Kiran Bajaj

и другие.

Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(23)

Опубликована: Авг. 23, 2024

A direct ortho-Csp

Язык: Английский

Процитировано

1

Efficient synthesis of spirooxazine-pyrans via rhodium-catalyzed [3+3] cascade spiroannulation of benzoxazines with 1-diazonaphthalen-2(1H)-ones DOI

Junwei Huang,

Xuelin Yue,

Yijie Gao

и другие.

New Journal of Chemistry, Год журнала: 2023, Номер 47(30), С. 14430 - 14435

Опубликована: Янв. 1, 2023

A redox-neutral access to spirooxazine-pyrans has been realized via Rh( iii )-catalysed [3+3] cascade spirocyclization of benzo[ b ][1,4]oxazines and 1-diazonaphthalen-2(1 H )-ones under extremely mild reaction conditions.

Язык: Английский

Процитировано

3

Recent Progress in Transition Metal-Catalyzed C—H Bond Activation of N-Aryl Phthalazinones DOI Open Access

Haichun Gu,

Xinxin Jin, Jiaqi Li

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2022, Номер 42(9), С. 2682 - 2682

Опубликована: Янв. 1, 2022

Язык: Английский

Процитировано

5

Rh(III)-catalyzed [5+1] spirocyclization to produce novel benzimidazole-incorporated spirosuccinimides DOI Creative Commons

Wei-Yi Pu,

Xinyi Chen, Lin Dong

и другие.

Green Synthesis and Catalysis, Год журнала: 2022, Номер 4(4), С. 338 - 341

Опубликована: Сен. 29, 2022

Transition-metal-catalyzed cross-coupling reactions as very efficient and atom-economical approaches have been widely used to build up complex heterocyclic compounds. However, modification of 2-oxyl benzimidazole skeleton using maleimide compounds via C–H activation has remained unprecedented. Herein, we developed a rhodium(III)-catalyzed [5 ​+ ​1] cascade spiroannulation construct diversified novel benzimidazole-incorporated spirosuccinimide derivatives from benzimidazoles maleimides.

Язык: Английский

Процитировано

2