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

被引：22

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

[21] Catalytic [2+2+1] Synthesis of Fused Thiophenes Using Thiocarbonyls as Sulfur Donors [J].

Matsui, Kazuma ;

Shibuya, Masatoshi ;

Yamamoto, Yoshihiko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (49) :15397-15400

[22] SYNTHESIS OF THE PYRROLIDINE RING-SYSTEM BY RADICAL CYCLIZATION [J].

PADWA, A ;

NIMMESGERN, H ;

WONG, GSK .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5620-5627

[23] Poly(3,4-ethylenedioxyselenophene) [J].

Patra, Asit ;

Wijsboom, Yair H. ;

Zade, Sanjio S. ;

Li, Mao ;

Sheynin, Yana ;

Leitus, Gregory ;

Bendikov, Michael .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (21) :6734-+

[24]

Peripichlca I. F., 2009, HDB THIOPHENE BASED, V1

[25]

Peripichlca I. F., 2009, HDB THIOPHENE BASED, V2

[26] Iron(II)-catalysed [2+2+2] cycloaddition for pyridine ring construction [J].

Richard, Vincent ;

Ipouck, Melinda ;

Merel, Delphine S. ;

Gaillard, Sylvain ;

Whitby, Richard J. ;

Witulski, Bernhard ;

Renaud, Jean-Luc .

CHEMICAL COMMUNICATIONS, 2014, 50 (05) :593-595

[27] CONJUGATED POLY(THIOPHENES) - SYNTHESIS, FUNCTIONALIZATION, AND APPLICATIONS [J].

RONCALI, J .

CHEMICAL REVIEWS, 1992, 92 (04) :711-738

[28] REDUCTION OF THE STERIC HINDRANCE TO CONJUGATION IN 3,4-DISUBSTITUTED POLY(THIOPHENES) - CYCLOPENTA[C]THIOPHENE AND THIENO[C]THIOPHENE AS PRECURSORS OF ELECTROGENERATED CONDUCTING POLYMERS [J].

RONCALI, J ;

GARNIER, F ;

GARREAU, R ;

LEMAIRE, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (19) :1500-1502

[29]

Rosemeyer H., 2013, HELV CHIM ACTA, V96, P201

[30] Intramolecular Transannulation of Alkynyl Triazoles via Alkyne-Carbene Metathesis Step: Access to Fused Pyrroles [J].

Shi, Yi ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2013, 15 (20) :5394-5396

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