Umpolung of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienones for the regiodivergent synthesis of disubstituted catechols

被引：0

作者：

Akazawa, Ryunosuke ^{[1
]}

Mohamed, Ahmed A. B. ^{[1
,2
]}

Yahata, Kenzo ^{[1
]}

Miyagaki, Kohei ^{[1
]}

Togami, Masaki ^{[1
]}

Sawama, Yoshinari ^{[1
]}

Kanomata, Kyohei ^{[1
]}

Akai, Shuji ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

[2] Mansoura Univ, Fac Pharm, Dept Med Chem, Mansoura 35516, Dakahlia, Egypt

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2024年 / 97卷 / 11期

关键词：

catechols; hypervalent iodine reagent; rearrangement; POLYCYCLIC AROMATIC-HYDROCARBONS; DERIVATIVES; QUINONES;

D O I：

10.1093/bulcsj/uoae111

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The umpolung of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienones 1 with PhI(OCOCF3)(2) achieved the migration into the more electron-rich C3 position, providing exclusively 3,4-disubstituted catechols 3. Acid-induced rearrangement of 1 produced 4,5-disubstituted catechols 2. These two reactions enabled the highly selective production of two regioisomers of disubstituted catechols, especially biaryls containing catechol moieties, from the common intermediates 1.

引用

页数：6

共 50 条

[21] Nucleophilic additions to 4,4-disubstituted 2,5-cyclohexadienones: Can dipole effects control facial selectivity?
Wipf, P
Jung, JK
CHEMICAL REVIEWS, 1999, 99 (05) : 1469 - 1480
[22] USE OF 2,5-DICHLOROTHIOPHENE IN SYNTHESIS OF 3,4-DISUBSTITUTED THIOPHENES
MACDOWELL, DW
PATRICK, TB
FRAME, BK
ELLISON, DL
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (04): : 1226 - +
[23] Synthesis and inclusion complexation studies of a novel molecular receptor for 1,4-disubstituted benzenes and 4,4'-disubstituted biphenyls.
Macias, AT
Kumar, KA
Marchand, AP
Evanseck, JD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U603 - U603
[24] THE USE OF 4,4-DISUBSTITUTED NOPINONES FOR NATURAL-PRODUCT SYNTHESIS - SYNTHESIS OF ELEMANOID SESQUITERPENES
KATO, M
WATANABE, M
VOGLER, B
AWEN, BZ
MASUDA, Y
TOOYAMA, Y
YOSHIKOSHI, A
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25): : 7071 - 7076
[25] AN ASYMMETRIC-SYNTHESIS OF CHIRAL 4,4-DISUBSTITUTED CYCLOHEXENONES IN HIGH ENANTIOMERIC PURITY
MEYERS, AI
LEFKER, BA
WANNER, KT
AITKEN, RA
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10): : 1936 - 1938
[26] SYNTHESIS, PHARMACOLOGICAL EFFECTS, AND CONFORMATION OF 4,4-DISUBSTITUTED 1,4-DIHYDROPYRIDINES
GOLDMANN, S
BORN, L
KAZDA, S
PITTEL, B
SCHRAMM, M
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) : 1413 - 1418
[27] EFFICIENT ASYMMETRIC-SYNTHESIS OF (+)-MESEMBRINE AND RELATED CHIRAL 4,4-DISUBSTITUTED CYCLOHEXANONES
MEYERS, AI
HANREICH, R
WANNER, KT
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) : 7776 - 7778
[28] Direct synthesis of 4,4-disubstituted N-silyl-1,4-dihydropyridines
Bräckow, J
Wanner, KT
TETRAHEDRON, 2006, 62 (10) : 2395 - 2404
[29] Computational studies of inclusion phenomena and synthesis of a novel and selective molecular receptor for 1,4-disubstituted benzenes and 4,4′-disubstituted biphenyls
Macias, AT
Kumar, KA
Marchand, AP
Evanseck, JD
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07): : 2083 - 2089
[30] Synthesis, Urease and Acetylcholine Esterase Inhibition Activities of Some 1,4-Disubstituted Thiosemicarbazides and their 2,5-Disubstituted Thiadiazoles
Saleem, Muhammad
Rafiq, Muhammad
Hanif, Muhammad
Rama, Nasim Hasan
Seo, Sung-Yum
Lee, Ki-Hwan
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (08): : 2741 - 2747

← 1 2 3 4 5 →