Synthesis and Chemical Reactivity of New Azaenamines Incorporated the 4,5,6,7-Tetrahydrobenzo[b]thiophene Moiety: 3+3 Atom Combination

被引：45

作者：

Abdelhamid, Ismail Abdelshafy ^{[1
,2
]}

Darwish, Elham Sayed ^{[1
]}

Nasra, Miead Adel ^{[1
]}

Abdel-Gallil, Fathy Mohamed ^{[1
]}

Fleita, Daisy Hanna ^{[3
]}

机构：

[1] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt

[2] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany

[3] Amer Univ Cairo, Dept Chem, Cairo, Egypt

来源：

SYNTHESIS-STUTTGART | 2010年 / 07期

关键词：

azaenamine; tetrahydrobenzo[b]thiophene; Michael addition; condensation; Mannich alkylation; MANNICH-TYPE REACTION; DERIVATIVES; PYRIDAZINES; CHITOSAN; CATALYST; AMINES; ACID;

D O I：

10.1055/s-0029-1219235

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel azaenamines incorporating a tetrahydrothiophene moiety were prepared. Michael addition of an azaenamine with alpha,beta-unsaturated nitriles took place to give [1]benzothieno[3',2':5,6]pyrimido[1,2-b]pyridazine (thia- triaza-benzo[a]fluorene) derivatives. The condensation with malononitrile resulted in the formation of a [1]benzothieno[3',2':5,6]pyrimido[1,2-b]pyridazine-4-carbonitrile. The azaenamine also reacted with aldehydes and piperidine to give Mannich products.

引用

页码：1107 / 1112

页数：6

共 50 条

[1] SYNTHESIS AND ANTIVIRAL ACTIVITY OF 7-OXY-4,5,6,7-TETRAHYDROBENZO[B] THIOPHENE AND 7-HYDROXY-4,5,6,7-TETRAHYDROBENZO[B] THIOPHENE
KAPUSTINA, MV
KHARIZOMENOVA, IA
SHVEDOV, VI
FOMINA, AN
NIKOLAYEVA, IS
GOLOVANOVA, YA
BOGDANOVA, GA
ALEKSEEVA, LM
KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1990, 24 (04): : 39 - 40
[2] Synthesis of 4,5,6,7-tetrahydrobenzo [b] thiophene based azo disperse dyes
Naik, SJ
Halkar, UP
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 15 (03) : 213 - 216
[3] SYNTHESIS OF 3-HETARYL-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENES
SABNIS, RW
RANGNEKAR, DW
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (04) : 1027 - 1029
[4] Photooxygenation of 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene
Altundas, R
Krawiec, M
Watson, WH
Balci, M
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 1997, 27 (11) : 645 - 648
[5] 2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile
Silva, Willams L.
de Lima, Maria do Carmo A.
Galdino, Suely L.
Pitta, Ivan R.
De Simone, Carlos A.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O3161 - U836
[6] 2-salicylideneamino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile
Elerman, Y
Elmali, A
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1998, 54 : 529 - 531
[7] Photooxygenation of 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene
Ramazan Altundas
Mariusz Krawiec
William H. Watson
Metin Balci
Journal of Chemical Crystallography, 1997, 27 : 645 - 648
[8] A new and facile synthesis of methyl 3-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylate
Tenora, Lukas
Buchlovic, Marian
Man, Stanislav
Potacek, Milan
TETRAHEDRON LETTERS, 2011, 52 (03) : 401 - 403
[9] Reaction of 3-Cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene with Enaminonitriles
Rafat M. Mohareb
Fatma A. Al-Omran
Jonathan Z. Ho
Monatshefte für Chemie / Chemical Monthly, 2002, 133 : 1443 - 1452
[10] PREPARATION AND REACTIONS OF 2-ISOTHIOCYANATO-3-CYANO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE
PAZDERA, P
REZKA, M
NOVACEK, E
CHEMICAL PAPERS, 1990, 44 (01): : 63 - 69

← 1 2 3 4 5 →