PREPARATION OF NEW NITROGEN-BRIDGED HETEROCYCLES. 68. ONE-POT SYNTHSIS OF 4-SUBSTITUTED 5-ACYLTHIENO[3,2-d]THIAZOLE DERIVATIVES

被引：5

作者：

Kakehi, Akikazu ^{[1
]}

Suga, Hiroyuki ^{[1
]}

Okumura, Yukihisa ^{[1
]}

Nishi, Takashi ^{[1
]}

机构：

[1] Shinshu Univ, Fac Engn, Dept Chem & Mat Engn, Nagano 3808553, Japan

来源：

HETEROCYCLES | 2010年 / 81卷 / 01期

关键词：

Thieno[3,2-d]thiazole; Synthesis; 3-(1-Pyridinio)thiophene-2-thiolate; Dimethyl Acetylenedicarboxylate; X-Ray Analysis;

D O I：

10.3987/COM-09-11852

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of 5-acyl-3-(1-pyridinio)thiophene-2-thiolates with dimethyl acetylenedicarboxylate in xylene at the reflux temperature afforded the corresponding 2-unsubstituted 5-acylthieno[3,2-d]thiazoles in 25-69% yields together with dimethyl phthalate as another fragmentation product. In a few reactions, the unexpected products, dimethyl 2-[2-acylthieno[2',3':2,3]-1,4-thiazino[4,5-a]pyrrol-8-ylidene]succinate derivatives, were also isolated, though their yields were very low.

引用

页码：175 / 184

页数：10

共 15 条

[1] PREPARATION OF NEW NITROGEN-BRIDGED HETEROCYCLES .39. ONE-POT SYNTHESIS OF 2H-PYRANO[3,2-A]INDOLIZIN-2-ONE DERIVATIVES
KAKEHI, A
ITO, S
MATSUBARA, K
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (08) : 2409 - 2415
[2] Preparation of new nitrogen-bridged heterocycles .43. Synthesis and reaction of 5aH-pyrido [1,2-d][1,3,4] thiadiazepine derivatives
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JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22): : 7788 - 7793
[3] PREPARATION OF NEW NITROGEN-BRIDGED HETEROCYCLES. 63. UNEXPECTED FORMATION OF THIENO[3′,4′:4,5]IMIDAZO[1,2-a]-PYRIDINES
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Suga, Hiroyuki
Izumita, Atsushi
Abe, Takashi
HETEROCYCLES, 2008, 76 (01) : 391 - 399
[4] PREPARATION OF NEW NITROGEN-BRIDGED HETEROCYCLES .35. SMOOTH SYNTHESIS OF 10AH-PYRIDO[1,2-D][1,4]THIAZEPINE DERIVATIVES
KAKEHI, A
ITO, S
HAKUI, J
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (11) : 3475 - 3482
[5] Preparation of New Nitrogen-Bridged Heterocycles 72. A New Approach to 1-Acyl-3-(substituted methylthio)thieno[3′,4′:4,5]imidazo[1,5-a]-pyridine Derivatives
Kakehi, Akikazu
Suga, Hiroyuki
Okumura, Yukihisa
Itoh, Kennosuke
Kobayashi, Kouji
Aikawa, Yoshihiro
Misawa, Kotaro
CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (11) : 1502 - 1510
[6] One-Pot Synthesis of Thieno[2,3-b]pyridine and Pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine Derivatives
I. V. Dyachenko
V. D. Dyachenko
P. V. Dorovatovsky
V. N. Khrustalev
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Russian Journal of Organic Chemistry, 2020, 56 : 974 - 982
[7] One-Pot Synthesis of Thieno[2,3-b]pyridine and Pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine Derivatives
Dyachenko, I. V.
Dyachenko, V. D.
Dorovatovsky, P. V.
Khrustalev, V. N.
Nenajdenko, V. G.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (06) : 974 - 982
[8] PREPARATION OF NEW NITROGEN-BRIDGED HETEROCYCLES .29. REINVESTIGATION ON THE DEHYDROGENATION REACTION OF 5,5A-DIHYDROPYRIDO[2,1-C]THIENO[3,2-E][1,4]THIAZINE DERIVATIVES
KAKEHI, A
ITO, S
HAKUI, J
FUKAZAWA, H
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (05) : 1244 - 1251
[9] An efficient one-pot three-step domino synthesis of substituted bis(pyrazino[2′,3′:4,5]thieno[3,2-d]pyrimidin-4(3H)-ones)
Blanco, Gerardo
Fernandez-Mato, Antonio
Quintela, Jose M.
Peinador, Carlos
TETRAHEDRON, 2008, 64 (49) : 11136 - 11143
[10] SYNTHESIS OF NEW HETEROCYCLES WITH DICOORDINATED PHOSPHORUS - 3-SUBSTITUTED THIAZOLO[3,2-D][1,4,2]DIAZAPHOSPHOLE AND ITS 5,6-DIHYDRO AND BENZO DERIVATIVES
BANSAL, RK
MAHNOT, R
SHARMA, DC
KARAGHIOSOFF, K
SYNTHESIS-STUTTGART, 1992, (03): : 267 - 269

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