Pyridazine N-Oxides as Precursors of Metallocarbenes: Rhodium-Catalyzed Transannulation with Pyrroles

被引：33

作者：

Kanchupalli, Vinaykumar ^{[1
]}

Joseph, Desna ^{[1
]}

Katukojvala, Sreenivas ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res, Dept Chem, Bhopal 462066, Madhya Pradesh, India

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 23期

关键词：

ENALCARBENOIDS DIRECT SYNTHESIS; TERMINAL ALKYNES; DENITROGENATIVE ANNULATION; MULTICOMPONENT REACTIONS; SATURATED HETEROCYCLES; EFFICIENT SYNTHESIS; AZAVINYL CARBENES; FACILE SYNTHESIS; INDOLES; FUNCTIONALIZATION;

D O I：

10.1021/acs.orglett.5b03064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyridazine N-oxides are used for the first time as precursors of metallocarbenes. These nitrogen-rich heterocycles led to the discovery of a novel acceptor and donor-acceptor enalcarbenoids. The synthetic utility of these metallocarbenes was demonstrated in the rhodium-catalyzed denitrogenative transannulation of pyridazine N-oxides with pyrroles to the valuable alkyl, 7-aryl, and 7-styryl indoles. The transannulation strategy was applied to the synthesis of a potent anticancer agent.

引用

页码：5878 / 5881

页数：4

共 50 条

[41] Regioselective Synthesis of Dihydrothiophenes and Thiophenes via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Alkenes
Son, Jeong-Yu
Kim, Jonghye
Han, Sang Hoon
Kim, Sung Hong
Lee, Phil Ho
ORGANIC LETTERS, 2016, 18 (20) : 5408 - 5411
[42] Synthesis of benzothiazonine by rhodium-catalyzed denitrogenative transannulation of 1-sulfonyl-1,2,3-triazole and thiochromone
Jablasone, Saygbechi T.
Ye, Zihang
Duan, Shengguo
Xu, Ze-Feng
Li, Chuan-Ying
Xu, Ze-Feng (xuzefeng@zstu.edu.cn), 1600, Royal Society of Chemistry (19): : 5758 - 5761
[43] Synthesis of benzothiazonine by rhodium-catalyzed denitrogenative transannulation of 1-sulfonyl-1,2,3-triazole and thiochromone
Jablasone, Saygbechi T., Jr.
Ye, Zihang
Duan, Shengguo
Xu, Ze-Feng
Li, Chuan-Ying
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (26) : 5758 - 5761
[44] Synthesis of Nitrogen Heterocycles via Photochemical Ring Opening of Pyridazine N-Oxides
Portillo, Maribel
Maxwell, Michael A.
Frederich, James H.
ORGANIC LETTERS, 2016, 18 (19) : 5142 - 5145
[45] Experimental and theoretical molecular and electronic structures of the N-oxides of pyridazine, pyrimidine and pyrazine
Aitken, R. Alan
Fodi, Bernd
Palmer, Michael H.
Slawin, Alexandra M. Z.
Yang, Jing
TETRAHEDRON, 2012, 68 (29) : 5845 - 5851
[46] Synthesizing Silyl Arylsulfonyl Hydrazones as Silyldiazomethane Precursors and Their Use in Rhodium-Catalyzed Reactions
Tsuruda, Shuji
Saito, Keigo
Matsuzaki, Tsuyoshi
Zhou, Da-Yang
Suzuki, Takeyuki
Sako, Makoto
Arisawa, Mitsuhiro
Murai, Kenichi
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (10) : 2305 - 2311
[47] Carboxamide oximes as convenient precursors for the synthesis of pyrimidine N-oxides
Mlakar, B
Stefane, B
Kocevar, M
Polanc, S
TETRAHEDRON, 1998, 54 (17) : 4387 - 4396
[48] Deoxygenation of N-oxides with triphenylphosphine, catalyzed by dichlorodioxomolybdenum(VI)
Sanz, R
Escribano, J
Fernández, Y
Aguado, R
Pedrosa, MR
Arnáiz, FJ
SYNLETT, 2005, (09) : 1389 - 1392
[49] Rhodium-Catalyzed Enantioposition-Selective Hydroarylation of Divinylphosphine Oxides with Aryl Boroxines
Wang, Zhe
Hayashi, Tamio
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (06) : 1702 - 1706
[50] New chiral α-aminophosphine oxides and sulfides:: an unprecedented rhodium-catalyzed ligand epimerization
Andrieu, J
Camus, JM
Poli, R
Richard, P
NEW JOURNAL OF CHEMISTRY, 2001, 25 (08) : 1015 - 1023

← 1 2 3 4 5 →