Sulfinates and thiocyanates triggered 6-endo cyclization of o-alkynylisocyanobenzenes

被引：21

作者：

Khaikate, Onnicha

Meesin, Jatuporn

Pohmakotr, Manat

Reutrakul, Vichai

Leowanawat, Pawaret

Soorukram, Darunee

Kuhakarn, Chutima ^{[1
]}

机构：

[1] Mahidol Univ, Fac Sci, Dept Chem, Rama 6 Rd, Bangkok 10400, Thailand

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 44期

关键词：

QUINOLINE N-OXIDES; ONE-POT SYNTHESIS; INTRAMOLECULAR CYCLIZATION; CATALYZED SULFONYLATION; MEDIATED SULFONYLATION; ISOCYANIDE INSERTION; RADICAL CYCLIZATION; C2; SULFONYLATION; SULFUR-DIOXIDE; INHIBITORS;

D O I：

10.1039/c8ob02338g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diverse 2-sulfonyl- and 2-thiocyanato-3-substituted quinolines were synthesized from o-alkynylisocyanobenzenes by nucleophilic addition of the respective sulfinate sodium salts and ammonium thiocyanate to the isocyanide moiety followed by cyclization. The salient features of the methodology include metal-free, ambient temperature and mild reaction conditions, ease of reagent handling, and broad functional group tolerance.

引用

页码：8553 / 8558

页数：6

共 65 条

[1] A review on anticancer potential of bioactive heterocycle quinoline
Afzal, Obaid
Kumar, Suresh
Haider, Md Rafi
Ali, Md Rahmat
Kumar, Rajiv
Jaggi, Manu
Bawa, Sandhya
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 : 871 - 910
[2] Sulfinate derivatives: dual and versatile partners in organic synthesis
Aziz, Jessy
Messaoudi, Samir
Alami, Mouad
Hamze, Abdallah
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (48) : 9743 - 9759
[3] THIOL-MEDIATED FREE-RADICAL CYCLIZATION OF ALKENYL AND ALKYNYL ISOCYANIDES
BACHI, MD
BALANOV, A
BARNER, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) : 7752 - 7758
[4] Role of sulfur chirality in the chemical processes of biology
Bentley, R
[J]. CHEMICAL SOCIETY REVIEWS, 2005, 34 (07) : 609 - 624
[5] Catalytic enantioselective synthesis of flavanones and chromanones
Biddle, Margaret M.
Lin, Michael
Scheidt, Karl A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) : 3830 - +
[6] THE ORGANOSULFUR CHEMISTRY OF THE GENUS ALLIUM - IMPLICATIONS FOR THE ORGANIC-CHEMISTRY OF SULFUR
BLOCK, E
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1992, 31 (09) : 1135 - 1178
[7] Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts
Cacchi, S
Fabrizi, G
Goggiamani, A
Parisi, LM
Bernini, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) : 5608 - 5614
[8] 8-Aminoquinoline: A Powerful Directing Group in Metal-Catalyzed Direct Functionalization of C-H Bonds
Corbet, Matthieu
De Campo, Floryan
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) : 9896 - 9898
[9] Discovery of Potent, Selective, and Orally Bioavailable Alkynylphenoxyacetic Acid CRTH2 (DP2) Receptor Antagonists for the Treatment of Allergic Inflammatory Diseases
Crosignani, Stefano
Pretre, Adeline
Jorand-Lebrun, Catherine
Fraboulet, Gaele
Seenisamy, Jeyaprakashnarayanan
Augustine, John Kallikat
Missotten, Marc
Humbert, Yves
Cleva, Christophe
Abla, Nada
Daff, Hamina
Schott, Olivier
Schneider, Manfred
Burgat-Charvillon, Fabienne
Rivron, Delphine
Hamernig, Ingrid
Arrighi, Jean-Francois
Gaudet, Marilene
Zimmerli, Simone C.
Juillard, Pierre
Johnson, Zoe
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (20) : 7299 - 7317
[10] Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate
Du, Bingnan
Qian, Ping
Wang, Yang
Mei, Haibo
Han, Jianlin
Pan, Yi
[J]. ORGANIC LETTERS, 2016, 18 (16) : 4144 - 4147

← 1 2 3 4 5 6 7 →