AN EFFICIENT AND CONVENIENT SYNTHESIS OF 4,5,6,7-TETRAHYDROTHIENO[3,2-c]PYRIDINES BY A MODIFIED PICTET-SPENGLER REACTION VIA A FORMYLIMINIUM ION INTERMEDIATE

被引：3

作者：

Kitabatake, Michikazu ^{[1
]}

Hashimoto, Aki ^{[1
]}

Saitoh, Toshiaki ^{[1
]}

Sano, Takehiro ^{[1
]}

Mohri, Kunihiko ^{[1
]}

Horiguchi, Yoshie ^{[1
]}

机构：

[1] Showa Pharmaceut Univ, Tokyo 1948543, Japan

来源：

HETEROCYCLES | 2010年 / 81卷 / 08期

关键词：

4,5,6,7-Tetrahydrothieno[3,2-c]pyridine; Pictet-Spengler Reaction; Formyliminium Ion; Acid Catalyzed Cyclization; One Pot Procedure; TITANIUM(IV) ISOPROPOXIDE; 1,2,3,4-TETRAHYDROISOQUINOLINES; INHIBITORS;

D O I：

10.3987/COM-10-11992

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of N-formyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridines (5) was achieved in a highly efficient manner via trifluoroacetic acid catalyzed cyclization of formyliminium ion (4), which was produced by imination of 2-(2-thienyl)ethylamine (1) and a carbonyl compound (2) using titanium(IV) tetraisopropoxide followed by formylation with acetic-formic anhydride in a one-pot procedure. This modified Pictet-Spengler reaction provides a convenient method for preparing 4,5,6,7-tetahydrothieno[3,2-c]pyridines (6) possessing various substituents at C-4.

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页码：1903 / 1921

页数：19

相关论文

共 9 条

[1]

BRINGMANN G, 1991, COMPREHENSIVE ORGANI, V6, P736

[2] Synthesis of 4,5,6,7-tetrahydrothieno[3,2-c]pyridines and comparison with their isosteric 1,2,3,4-tetrahydroisoquinolines as inhibitors of phenylethanolamine N-methyltransferase [J].

Grunewald, Gary L. ;

Seim, Mitchell R. ;

Bhat, Seema R. ;

Wilson, Marc E. ;

Criscione, Kevin R. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (01) :542-559

[3] A facile synthsis of 1,1-disubstituted 1,2,3,4-tetrahydro-β-carbolines via trifluoroacetic acid catalyzed Pictet-Spengler reaction using titanium(IV) isopropoxide as an imination reagent [J].

Horiguchi, Y ;

Nakamura, M ;

Kida, A ;

Kodama, H ;

Saitoh, T ;

Sano, T .

HETEROCYCLES, 2003, 59 (02) :691-705

[4] A convenient synthesis of 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines via Pictet-Spengler reaction using titanium(IV) isopropoxide and acetic-formic anhydride [J].

Horiguchi, Y ;

Kodama, H ;

Nakamura, M ;

Yoshimura, T ;

Hanezi, K ;

Hamada, H ;

Saitoh, T ;

Sano, T .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (02) :253-257

[5] Facile synthesis and in vitro properties of 1-alkyl- and 1-alkyl-N-propargyl-1,2,3,4-tetrahydroisoquinoline derivatives on PC12 cells [J].

Kitabatake, Michikazu ;

Nagai, Junko ;

Abe, Kenji ;

Tsuchiya, Yukihiro ;

Ogawa, Keita ;

Yokoyama, Takashi ;

Mom, Kunihiko ;

Taguchi, Kyoji ;

Horiguchi, Yoshie .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (10) :4034-4043

[6] Glucose-6-phosphatase catalytic enzyme inhibitors:: Synthesis and in vitro evaluation of novel 4,5,6,7-tetrahydrothieno[3,2-c]- and -[2,3-c]pyridines [J].

Madsen, P ;

Lundbeck, JM ;

Jakobsen, P ;

Varming, AR ;

Westergaard, N .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (09) :2277-2289

[7] Facile preparation of N-methyl secondary amines by titanium(IV) isopropoxide-mediated reductive amination of carbonyl compounds [J].

Neidigh, KA ;

Avery, MA ;

Williamson, JS ;

Bhattacharyya, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (16) :2527-2531

[8]

Ohkubo M, 1996, CHEM PHARM BULL, V44, P778

[9] Prototype Pictet-Spengler reactions catalyzed by superacids. Involvement of dicationic superelectrophiles [J].

Yokoyama, A ;

Ohwada, T ;

Shudo, K .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) :611-617