Base-Catalyzed Addition of Ketones to Alkynes as a Key Step in the One-Pot Synthesis of 1-Formyl-2-pyrazolines

被引：7

作者：

Schmidt, Elena Yu. ^{[1
]}

Ivanova, Elena V. ^{[1
]}

Tatarinova, Inna V. ^{[1
]}

Semenova, Nadezhda V. ^{[1
]}

Ushakov, Igor A. ^{[1
]}

Trofimov, Boris A. ^{[1
]}

机构：

[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 09期

关键词：

ketones; alkynes; 1-formyl-2-pyrazolines; superbases; vinylation; STEREOSELECTIVE ALPHA-VINYLATION; BETA; GAMMA-UNSATURATED KETONES; CONVENIENT SYNTHESIS; PYRAZOLINE; ARYLACETYLENES; ANTICANCER; CHALCONES;

D O I：

10.1055/s-0034-1378687

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of ketones with alkynes in the presence of potassium tert-butoxide and dimethylsulfoxide followed by the treatment of the reaction mixture with hydrazine hydrate and formic acid leads to 2-pyrazoline-1-carbaldehydes in up to 81% yield.

引用

页码：1329 / 1336

页数：8

共 50 条

[1] Base-catalyzed α-vinylation of ketones with acetylenes as a key step in one-pot synthesis of pyrazolines and pyrazoles
Schmidt, Elena Yu
Ivanova, Elena V.
Semenova, Nadezhda V.
Tatarinova, Inna V.
Ushakov, Igor A.
Trofimov, Boris A.
MENDELEEV COMMUNICATIONS, 2015, 25 (02) : 131 - 132
[2] Base-Catalyzed One-Pot Synthesis of 2,3,6-Substituted Pyridines
Zhu, Baofu
He, Jiaming
Zou, Kai
Li, Anquan
Zhang, Chen
Zhao, Jiaji
Cao, Hua
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (16): : 11450 - 11459
[3] Base-Catalyzed One-Pot Synthesis of Selenosulfides: A Base Basicity-Controlled Approach
Lee, Sangik
Sim, Jaehee
Lee, Anna
JOURNAL OF ORGANIC CHEMISTRY, 2023, 89 (01): : 748 - 755
[4] ONE-POT BASE-CATALYZED CONDENSATION-REACTIONS OF ACTIVATED NITRILES AND 2-HYDROXY-1-NAPHTHALENECARBALDEHYDE WITH DIFFERENT KETONES
FADDA, AA
ZIMAITY, MT
GIRGES, MM
BIEHL, E
KHALID, HM
CHEMICAL PAPERS-CHEMICKE ZVESTI, 1994, 48 (04): : 252 - 256
[5] Base-catalyzed addition of ketones to alkynes as a springboard to cycloalka[c]pyrazoline-2-carbaldehydes
Elena Yu. Schmidt
Elena V. Ivanova
Inna V. Tatarinova
Igor A. Ushakov
Nadezhda I. Protsuk
Boris A. Trofimov
Chemistry of Heterocyclic Compounds, 2015, 51 : 242 - 245
[6] Base-catalyzed addition of ketones to alkynes as a springboard to cycloalka[c]pyrazoline-2-carbaldehydes
Schmidt, Elena Yu.
Ivanova, Elena V.
Tatarinova, Inna V.
Ushakov, Igor A.
Protsuk, Nadezhda I.
Trofimov, Boris A.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (03) : 242 - 245
[7] Synthesis, antiamoebic activity and thermal study of copper complexes of 1-formyl-2-pyrazolines
Pramod Singh
Jagmohan S. Negi
M. S. M. Rawat
Geeta Joshi nee Pant
Journal of Thermal Analysis and Calorimetry, 2013, 111 : 549 - 552
[8] Synthesis, antiamoebic activity and thermal study of copper complexes of 1-formyl-2-pyrazolines
Singh, Pramod
Negi, Jagmohan S.
Rawat, M. S. M.
Pant, Geeta Joshi Nee
JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, 2013, 111 (01) : 549 - 552
[9] Visible-light-assisted base-catalyzed, one-pot synthesis of highly functionalized cinnolines
Elkamhawy, Ahmed
Jaragh-Alhadad, Laila
Mekheimer, Ramadan Ahmed
Abdullah, Omeima
Abd-Elmonem, Mohamed
Moustafa, Moustafa Sherief
Abdel-Hameed, Afaf
Mohamed, Tahany Mahmoud
Sadek, Kamal Usef
GREEN PROCESSING AND SYNTHESIS, 2023, 12 (01)
[10] One-pot synthesis of α-hydroxy ketones from captodative formyl(amino)alkenes
Rulev, AY
Novokshonov, VV
Chuvashev, YA
Fedorov, SV
Larina, LI
MENDELEEV COMMUNICATIONS, 2003, (01) : 23 - 25

← 1 2 3 4 5 →