Tags

Type your tag names separated by a space and hit enter

Synthesis of pyrazolo[5,1-a]isoquinolines via a silver(I)-catalyzed reaction of (1-arylethylidene)hydrazides with N'-(2-alkynylbenzylidene)hydrazides.
Org Biomol Chem. 2015 Dec 28; 13(48):11657-62.OB

Abstract

A silver(I)-catalyzed reaction of (1-arylethylidene)hydrazides with N'-(2-alkynylbenzylidene)hydrazides is reported, which provides an efficient approach for the synthesis of pyrazolo[5,1-a]isoquinolines. During the reaction process, azo-alkene and isoquinolinium-2-yl amide acted as the key intermediates, which then underwent [3 + 2] cycloaddition and intramolecular rearrangement leading to the corresponding pyrazolo[5,1-a]isoquinolines. Azo-alkene would be formed in situ from (1-arylethylidene)hydrazide in the presence of I2 and TBHP, and isoquinolinium-2-yl amide would be generated in situ via a silver(I)-promoted 6-endo cyclization of N'-(2-alkynylbenzylidene)hydrazide. This transformation proceeds smoothly under mild conditions and tolerates a broad range of functional groups.

Authors+Show Affiliations

Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China. jie_wu@fudan.edu.cn.No affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26468943

Citation

Gong, Xinxing, and Jie Wu. "Synthesis of Pyrazolo[5,1-a]isoquinolines Via a silver(I)-catalyzed Reaction of (1-arylethylidene)hydrazides With N'-(2-alkynylbenzylidene)hydrazides." Organic & Biomolecular Chemistry, vol. 13, no. 48, 2015, pp. 11657-62.
Gong X, Wu J. Synthesis of pyrazolo[5,1-a]isoquinolines via a silver(I)-catalyzed reaction of (1-arylethylidene)hydrazides with N'-(2-alkynylbenzylidene)hydrazides. Org Biomol Chem. 2015;13(48):11657-62.
Gong, X., & Wu, J. (2015). Synthesis of pyrazolo[5,1-a]isoquinolines via a silver(I)-catalyzed reaction of (1-arylethylidene)hydrazides with N'-(2-alkynylbenzylidene)hydrazides. Organic & Biomolecular Chemistry, 13(48), 11657-62. https://doi.org/10.1039/c5ob01972a
Gong X, Wu J. Synthesis of Pyrazolo[5,1-a]isoquinolines Via a silver(I)-catalyzed Reaction of (1-arylethylidene)hydrazides With N'-(2-alkynylbenzylidene)hydrazides. Org Biomol Chem. 2015 Dec 28;13(48):11657-62. PubMed PMID: 26468943.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of pyrazolo[5,1-a]isoquinolines via a silver(I)-catalyzed reaction of (1-arylethylidene)hydrazides with N'-(2-alkynylbenzylidene)hydrazides. AU - Gong,Xinxing, AU - Wu,Jie, Y1 - 2015/10/15/ PY - 2015/10/16/entrez PY - 2015/10/16/pubmed PY - 2015/10/16/medline SP - 11657 EP - 62 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 13 IS - 48 N2 - A silver(I)-catalyzed reaction of (1-arylethylidene)hydrazides with N'-(2-alkynylbenzylidene)hydrazides is reported, which provides an efficient approach for the synthesis of pyrazolo[5,1-a]isoquinolines. During the reaction process, azo-alkene and isoquinolinium-2-yl amide acted as the key intermediates, which then underwent [3 + 2] cycloaddition and intramolecular rearrangement leading to the corresponding pyrazolo[5,1-a]isoquinolines. Azo-alkene would be formed in situ from (1-arylethylidene)hydrazide in the presence of I2 and TBHP, and isoquinolinium-2-yl amide would be generated in situ via a silver(I)-promoted 6-endo cyclization of N'-(2-alkynylbenzylidene)hydrazide. This transformation proceeds smoothly under mild conditions and tolerates a broad range of functional groups. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/26468943/Synthesis_of_pyrazolo[51_a]isoquinolines_via_a_silver_I__catalyzed_reaction_of__1_arylethylidene_hydrazides_with_N'__2_alkynylbenzylidene_hydrazides_ L2 - https://doi.org/10.1039/c5ob01972a DB - PRIME DP - Unbound Medicine ER -
Try the Free App:
Prime PubMed app for iOS iPhone iPad
Prime PubMed app for Android
Prime PubMed is provided
free to individuals by:
Unbound Medicine.