Metal‐Free Dearomatization: Direct Access to Spiroindol(en)ines in Batch and Continuous‐Flow DOI
Prabhat Ranjan, Gerardo M. Ojeda‐Carralero, Upendra K. Sharma

и другие.

Chemistry - A European Journal, Год журнала: 2018, Номер 25(10), С. 2442 - 2446

Опубликована: Дек. 3, 2018

Abstract A metal‐free, phosphine‐catalyzed intramolecular “umpolung Michael addition” on alkynes to form spiroindol(en)ines is reported. This nucleophilic catalysis enables the formation of a wide scope five‐ and six‐membered in moderate excellent yields batch as well under continuous‐flow conditions. Triphenylphosphine‐catalyzed activation allows exclusive exo ‐product mild reaction

Язык: Английский

Gold(i)-catalyzed pathway-switchable tandem cycloisomerizations to indolizino[8,7-b]indole and indolo[2,3-a]quinolizine derivatives DOI
Chengjun Liu,

Zenghui Sun,

Fukai Xie

и другие.

Chemical Communications, Год журнала: 2019, Номер 55(96), С. 14418 - 14421

Опубликована: Янв. 1, 2019

Experimental and theoretical explorations were performed on the pathways of cascade cycloisomerizations tryptamine-N-ethynylpropiolamide substrates. The methodology provided a common strategy to access either indolizino[8,7-b]indoles or indolo[2,3-a]quinolizines in switchable fashion.

Язык: Английский

Процитировано

28

Synthesis of 3-(Organochalcogen) Chalcogenazolo Indoles via Cascade Cyclization of N-Alkynylindoles DOI

Thaís Prochnow,

Adriano Maroneze,

Davi F. Back

и другие.

The Journal of Organic Chemistry, Год журнала: 2019, Номер 84(5), С. 2891 - 2900

Опубликована: Янв. 31, 2019

A transition metal-free one-pot, three-steps protocol combining N-alkynylindoles, n-butyllithium, elemental selenium, and an electrophile source was developed to allow the synthesis of 3-(organoselanyl) selenazolo indoles. Substrate scope studied by varying structure N-alkynylindoles source. This sequential reaction proceeded selectively through initial intramolecular 5- endo-dig mode with two new carbon-selenium bonds formation in a one-pot procedure. The conditions were also compatible sulfur tellurium, which led construct 3-(alkylthio) thiazolo indoles 3-(alkyltelluro) tellurazolo indoles, respectively. In addition, it demonstrated that series dichalcogenides derived from chalcogenazoloindoles ring could be easily prepared via oxidation chalcogenolate anion contact air.

Язык: Английский

Процитировано

26

Silver(I) Triflate‐Catalyzed Protocol for the Post‐Ugi Synthesis of Spiroindolines DOI

Manzoor Zaman,

Muhammad Hasan, Anatoly A. Peshkov

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2019, Номер 362(1), С. 261 - 268

Опубликована: Ноя. 2, 2019

Abstract A silver(I) triflate‐catalyzed protocol for the post‐Ugi synthesis of tetracyclic spiroindolines has been developed. The worked best indole‐3‐carbaldehyde‐derived Ugi adducts obtained using anilines and 3‐aryl propiolic acids. Thus, it is complementary to previous cationic gold‐catalyzed procedure that was developed analogues substrates derived from aliphatic amines 3‐alkyl Furthermore, we have demonstrated under our new settings this domino Friedel‐Crafts ipso cyclization / imine trapping process could be efficiently combined with preceding four‐component reaction into a two‐step one‐pot transformation. magnified image

Язык: Английский

Процитировано

26

Concise Synthesis of Spiro[indoline‐3,2′‐pyrrolidine] and 1‐Azacarbazole Derivatives via Copper‐Catalyzed Cyclization of Indoles DOI
Pengfei Wang, Chao Chen, Hui Chen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2017, Номер 359(14), С. 2339 - 2344

Опубликована: Апрель 21, 2017

Abstract A high‐yielding, copper‐catalyzed dearomatization reaction of indole from 2‐methylindole‐derived oxime acetates was realized, providing access to structurally novel spiro[indoline‐3,2′‐pyrrolidine] derivatives in 67–98% yields. When the C‐2 position not substituted, azacarbazole were obtained moderate This transformation provides an efficient approach nitrogen‐containing spiroindolenine and with wide substrate scope. magnified image

Язык: Английский

Процитировано

27

Metal‐Free Dearomatization: Direct Access to Spiroindol(en)ines in Batch and Continuous‐Flow DOI
Prabhat Ranjan, Gerardo M. Ojeda‐Carralero, Upendra K. Sharma

и другие.

Chemistry - A European Journal, Год журнала: 2018, Номер 25(10), С. 2442 - 2446

Опубликована: Дек. 3, 2018

Abstract A metal‐free, phosphine‐catalyzed intramolecular “umpolung Michael addition” on alkynes to form spiroindol(en)ines is reported. This nucleophilic catalysis enables the formation of a wide scope five‐ and six‐membered in moderate excellent yields batch as well under continuous‐flow conditions. Triphenylphosphine‐catalyzed activation allows exclusive exo ‐product mild reaction

Язык: Английский

Процитировано

27