A study of the Willgerodt-Kindler reaction to obtain thioamides and α-ketothioamides under solvent-less conditions

被引：24

作者：

Ernesto Valdez-Rojas, Jose ^{[1
]}

Rios-Guerra, Hulme ^{[1
]}

Leticia Ramirez-Sanchez, Alma ^{[1
]}

Garcia-Gonzalez, Guadalupe ^{[1
]}

Alvarez-Toledano, Cecilio ^{[2
]}

Guadalupe Lopez-Cortes, Jose ^{[2
]}

Toscano, Ruben A. ^{[2
]}

Guillermo Penieres-Carrillo, Jose ^{[1
]}

机构：

[1] Univ Nacl Autonoma Mexico, Secc Quim Organ, FESC, Fac Estudios Super Cuautitlan, Cuautitlan 54740, Izcalli, Mexico

[2] Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2012年 / 90卷 / 07期

关键词：

Willgerodt-Kindler modification; alpha-ketothioamides; solvent-less conditions; IR energy; noncatalyst; KNOEVENAGEL CONDENSATION; MECHANISM; ACIDS;

D O I：

10.1139/V2012-030

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this paper, the results obtained in the synthesis of thioamides and alpha-ketothioamides by a modification of the Willgerodt-Kindler reaction, under solvent-free and noncatalyst conditions using IR energy as a source of activation, are presented. The use of IR energy in these reactions has been shown to lead to a mixture of thioamide and alpha-ketothioamide as the main products in most cases, with the latter predominating. The yields of alpha-ketothioamides from most of these reactions are better than those reported previously. To the best of our knowledge, this is the first time that IR energy has been applied to promote the Willgerodt-Kindler reaction.

引用

页码：567 / 573

页数：7

共 39 条

[1] Synthesis of α-Ketothioamides via Willgerodt-Kindler Reaction of Arylglyoxals with Amines and Sulfur under Solvent-Free Conditions
Eftekhari-Sis, Bagher
Khajeh, Saleh Vahdati
Buyukgungor, Orhan
SYNLETT, 2013, 24 (08) : 977 - 980
[2] AN ALTERNATIVE METHOD FOR THE HYDROLYSIS OF THIOAMIDES IN THE WILLGERODT-KINDLER REACTION
ROGERS, MAT
JOURNAL OF THE CHEMICAL SOCIETY, 1950, (NOV): : 3350 - 3350
[3] A domino annulation reaction under Willgerodt-Kindler conditions
Kadzimirsz, Daniel
Kramer, Daniel
Sripanom, Lertnarong
Oppel, Iris M.
Rodziewicz, Pawel
Doltsinis, Nikos L.
Dyker, Gerald
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12): : 4644 - 4649
[4] Interesting behavior of acetone under the Willgerodt-Kindler reaction conditions
Darabi, HR
Aghapoor, K
Nakhshab, L
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2004, 59 (05): : 601 - 605
[5] PREPARATION OF N-UNSUBSTITUTED THIOAMIDES BY A MODIFIED WILLGERODT-KINDLER REACTION
YOU, QD
ZHOU, HY
WANG, QZ
LEI, XH
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1991, 23 (04) : 435 - 438
[6] Microwave-assisted rapid hydrolysis and preparation of thioamides by Willgerodt-Kindler reaction
Moghaddam, FM
Ghaffarzadeh, M
SYNTHETIC COMMUNICATIONS, 2001, 31 (02) : 317 - 321
[7] Primary amines in the Willgerodt-Kindler reaction: An efficient conversIon of aromatic aldehydes to thioamides
Kanyonyo, MR
Gozzo, A
Lambert, DM
Lesieur, D
Poupaert, JH
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1997, 106 (01): : 39 - 45
[8] The different, but interesting behaviors of benzyl systems in the Willgerodt-Kindler reaction under solvent-free conditions
Aghapoor, K
Darabi, HR
Tabar-Heydar, K
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (05) : 1183 - 1187
[9] Willgerodt-Kindler reaction of arylglyoxals with amines and sulfur in aqueous media: a simple and efficient synthesis of α-ketothioamides
Eftekhari-Sis, Bagher
Vahdati-Khajeh, Saleh
Amini, S. Motahhareh
Zirak, Maryam
Saraei, Mahnaz
JOURNAL OF SULFUR CHEMISTRY, 2013, 34 (05) : 464 - 473
[10] An expedient synthesis of thienylacetic acids using the Willgerodt-Kindler reaction under PTC conditions
Podshibyakin, Vitaly A.
Shepelenko, Evgenii N.
Tikhomirova, Karina S.
Dubonosov, Alexander D.
Bren, Vladimir A.
Minkin, Vladimir I.
ARKIVOC, 2016, : 72 - 78

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