Synthesis of 6H-thieno[3,2-b]pyridin-7-ones from N-(2-X-carbonyl)-3-thienyl ketenimines (X = RS, ArO, R2N) via consecutive [1,5]-X sigmatropic rearrangement and 6π-electrocyclization

被引：4
作者：
Alajarin, Mateo [1 ]
Vidal, Angel [1 ]
Ortin, Maria-Mar [1 ]
机构：
[1] Univ Murcia, Fac Quim, Dept Quim Organ, Murcia 30100, Spain
来源：
SYNTHESIS-STUTTGART | 2007年 / 04期
关键词：
azides; ketenimines; rearrangements; ketenes; thienopyridines;
D O I：
10.1055/s-2007-965874
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-(2-X-Carbonyl)-3-thienyl ketenimines (X = RS, ArO, R2N) undergo cyclization under thermal conditions, through a [1,5]X sigmatropic rearrangement followed by a 6 pi-electrocyclic ring closure of the resulting intermediate ketene, to provide 6H-thieno[3,2-b]pyridin-7-ones, bearing alkylthio, arylthio, aryloxy or amino groups at their 5-position.
引用
收藏
页码：590 / 596
页数：7
相关论文
共 54 条
[1]   From ketenimines to ketenes to quinolones:: Two consecutive pseudopericyclic events [J].
Alajarín, M ;
Ortín, MM ;
Sánchez-Andrada, P ;
Vidal, A ;
Bautista, D .
ORGANIC LETTERS, 2005, 7 (23) :5281-5284
[2]   Synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones by thermally induced cyclization of N-(2-benzyloxycarbonyl)phenyl ketenimines;: Oxygen-to-carbon migration of a benzyl group [J].
Alajarín, M ;
Vidal, A ;
Ortín, MM ;
Bautista, D .
SYNTHESIS-STUTTGART, 2005, (14) :2426-2432
[3]   Thermal cyclization of N-[2-(2-propenyl)-1-naphthyl] ketenimines:: intramolecular Diels-Alder reaction versus [1,5] hydrogen migration.: Synthesis of dibenz[b,h]acridines and benzo[h]quinolines [J].
Alajarín, M ;
Vidal, A ;
Ortín, MM .
TETRAHEDRON, 2005, 61 (32) :7613-7621
[4]   Mode selectivity in the intramolecular cyclization of ketenimines bearing N-acylimino units:: A computational and experimental study [J].
Alajarín, M ;
Sánchez-Andrada, P ;
Vidal, A ;
Tovar, F .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04) :1340-1349
[5]   The consecutive [2+2] cycloaddition-ring expansion route to diastereomeric 1,4-diazepin-5-ones from imino-ketenimines.: Alternative intramolecular transamidation of β-lactams [J].
Alajarín, M ;
Vidal, A ;
Tovar, F .
TETRAHEDRON, 2005, 61 (06) :1531-1537
[6]   Persistent radical effect in the intramolecular addition of benzylic radicals onto ketenimines:: selective cross-coupling of α-(indol-2-yl)benzyl radicals with the 1-cyano-1-methylethyl radical [J].
Alajarín, M ;
Vidal, A ;
Ortin, MM ;
Bautista, D .
NEW JOURNAL OF CHEMISTRY, 2004, 28 (05) :570-577
[7]   New persistent heteroarylmethyl radicals resulting from the intramolecular addition of aryloxymethyl radicals onto ketenimines.: Synthesis of 2H-1,4-benzoxazines [J].
Alajarín, M ;
Vidal, A ;
Ortín, MM ;
Bautista, D .
SYNLETT, 2004, (06) :991-994
[8]   Stereocontrolled synthesis of azeto[2,1-b] quinazolines bearing three stereocenters via the intramolecular [2+2] cycloaddition between ketenimines and imines [J].
Alajarín, M ;
Vidal, A ;
Tovar, F ;
de Arellano, MCR .
TETRAHEDRON-ASYMMETRY, 2004, 15 (03) :489-494
[9]   Intramolecular addition of benzylic radicals onto ketenimines.: Synthesis of 2-alkylindoles [J].
Alajarín, M ;
Vidal, A ;
Ortín, MM .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (23) :4282-4292
[10]   Ketenimine and imine functions linked by an ethylene group.: Intramolecular [4+2] cycloadditions leading to imidazo[1,2-b]isoquinolines [J].
Alajarín, M ;
Vidal, A ;
Tovar, F ;
Sánchez-Andrada, P ;
Bautista, D .
TETRAHEDRON, 2003, 59 (50) :9913-9918
123456