Radical-Cascade Avenue for 3,4-Fused-Ring-Substituted Thiophenes

被引：21

作者：

Agrawal, Abhijeet R. ^{[1
]}

Kumar, Neha Rani ^{[1
]}

Debnath, Sashi ^{[1
,2
,3
]}

Das, Sarasija ^{[1
]}

Kumar, Chandan ^{[1
]}

Zade, Sanjio S. ^{[1
]}

机构：

[1] IISER, Dept Chem Sci, Nadia 741246, W Bengal, India

[2] Univ Texas Southwestern Med Ctr Dallas, Dept Radiol, Clements Imaging Bldg,2201 Inwood Rd, Dallas, TX 75390 USA

[3] Univ Texas Southwestern Med Ctr Dallas, Adv Imaging Res Ctr, Clements Imaging Bldg,2201 Inwood Rd, Dallas, TX 75390 USA

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 16期

关键词：

ACYL RADICALS; SULFUR; CYCLIZATION; POLY(THIOPHENES); SUBSTITUTION; CONJUGATION; DERIVATIVES; GENERATION; POLYMERS; BOND;

D O I：

10.1021/acs.orglett.8b01577

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A single-step intramolecular radical cascade reaction of diynes and thioacetic acid in the presence of a catalytic amount of azobis(isobutyronitrile) as a radical initiator has been developed to synthesize thiophenes. This method allows easy and effective construction of a thiophene scaffold having 3,4-fused-ring substitution and unsubstituted 2,5-positions for further functionalization and polymerization. Using this method, derivatives of cyclopenta[c]thiophene, 3,4-ethylenedioxythiophene, and thiophene-containing spirocyclic compound have been synthesized.

引用

页码：4728 / 4731

页数：4

共 37 条

[1]

Anastas P., 1998, GREEN CHEM THEORY PR

[2] Synthesis of 3,4-ethylenedioxyselenophene (EDOS):: A novel building block for electron-rich π-conjugated polymers [J].

Aqad, E ;

Lakshmikantham, MV ;

Cava, MP .

ORGANIC LETTERS, 2001, 3 (26) :4283-4285

[3] The versatile thiophene: An overview of recent research on thiophene-based materials [J].

Barbarella, G ;

Melucci, M ;

Sotgiu, G .

ADVANCED MATERIALS, 2005, 17 (13) :1581-1593

[4]

Beckwith A. L. J., 1994, J CHEM SOC P2, V2, P1509

[5] Efficient synthesis of 3,4-ethylenedioxythiophenes (EDOT) by Mitsunobu reaction [J].

Caras-Quintero, D ;

Bäuerle, P .

CHEMICAL COMMUNICATIONS, 2002, (22) :2690-2691

[6] Chemistry of acyl radicals [J].

Chatgilialoglu, C ;

Crich, D ;

Komatsu, M ;

Ryu, I .

CHEMICAL REVIEWS, 1999, 99 (08) :1991-2069

[7] Generation and cyclization of acyl radicals from thiol esters under nonreducing, tin-free conditions [J].

Crich, D ;

Hao, XL .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5982-5988

[8] Generation of acyl radicals from thiolesters by intramolecular homolytic substitution at sulfur [J].

Crich, D ;

Yao, QW .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3566-3570

[9] METHYLENEDIOXYHETARENES, .1. PREPARATION OF 3,4-METHYLENEDIOXYTTHIOPHENE METHYLENEDIOXYFURAN, AND METHYLENEDIOXYPYRROLE DERIVATIVES [J].

DALLACKER, F ;

MUES, V .

CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (02) :569-575

[10] 3,4-Ethylenedioxythiophene and 3,4-Ethylenedioxyselenophene: Synthesis and Reactivity of Cα-Si Bond [J].

Das, Soumyajit ;

Dutta, Pradip Kumar ;

Panda, Snigdha ;

Zade, Sanjio S. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (14) :4868-4871

← 1 2 3 4 →