Synthesis of the novel thieno[4,3,2-ef][1,4]benzoxazepine ring system: 4,5-dihydro-3-(4-pyridinyl)thieno[4,3,2-ef][1,4]benzoxazepine maleate

被引：7

作者：

Tomer, JD ^{[1
]}

Shutske, GM ^{[1
]}

Friedrich, D ^{[1
]}

机构：

[1] Hoechst Mar Roussel Inc, Bridgewater, NJ 08807 USA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1997年 / 34卷 / 06期

关键词：

D O I：

10.1002/jhet.5570340621

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4,5-Dihydro-3-(4-pyridinyl)-thieno[4,3,2-ef][1,4]benzoxazepine maleate 2 has been synthesized from 3-amino-4-fluorobenzo[b]thiophene by employing an intramolecular nucleophilic aromatic fluoride displacement. In the presence of strong base and heat, 2 rearranges to form the isomeric hemiaminal, 3,4-dihydro-4-methyl-3-(4-pyridinyl)thieno[4,3,2-de][1,3] benzoxazine 10. A proposed mechanism for this rearrangement is discussed.

引用

页码：1769 / 1772

页数：4

共 50 条

[21] HETEROARENOBENZODIAZEPINES .2. SYNTHESIS OF 4H-THIENO[2,3-B] [1,4]-BENZODIAZEPIONES, [3,2-B] [1,4]-BENZODIAZEPIONES, AND [3,4-B] [1,4]-BENZODIAZEPINONES
CHAKRABARTI, JK
HOTTEN, TM
STEGGLES, DJ
TUPPER, DE
JOURNAL OF CHEMICAL RESEARCH-S, 1978, (11): : 428 - 429
[22] Efficient Synthesis of 1,3,4,5-Tetrahydropyrrolo-[4,3,2-de]quinoline
Synthetic Communications, 25 (05):
[23] EFFICIENT SYNTHESIS OF 1,3,4,5-TETRAHYDROPYRROLO[4,3,2-DE]QUINOLINE
ROUE, N
LEVY, J
BARRET, R
SYNTHETIC COMMUNICATIONS, 1995, 25 (05) : 681 - 690
[24] SYNTHESIS OF [1]BENZOTHIOPYRANO[4,3,2-DE]QUINOLINE
OKABAYASHI, I
FUJIWARA, H
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (04) : 733 - 735
[25] SYNTHESIS OF 4,5-DIHYDRO-1H,3H-THIENO[3,4-C]THIOPHENE AND 4,5-DIHYDRO-1H,3H-THIENO[3,4-C]FURAN
RIPOLL, JL
VALLEE, Y
KHALID, M
HAKIKI, A
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (07) : 1867 - 1868
[26] THE SYNTHESIS OF NOVEL POLYCYCLIC HETEROCYCLIC RING-SYSTEMS VIA PHOTOCYCLIZATION .15. [1]BENZOTHIENO[3',2'-4,5]THIENO[2,3-C]QUINOLINE, [1]BENZOTHIENO[3',2'-4,5]THIENO[2,3-C][1,2,4]TRIAZOLO[4-3-A]-QUINOLINE, [1]BENZOTHIENO[3',2'-4,5]THIENO[2,3-C]TETRAZOLO[1,5-A]QUINOLINE, THIENO[3',2'-4,5]THIENO[2-3-C][1,2,4]TRIAZOLO[4,3-A]QUINOLINE, AND THIENO[3',2'-4,5]THIENO[2,3-C]TETRAZOLO[1,5-A]QUINOLINE
LUO, JK
KUDO, H
FEDERSPIEL, RF
CASTLE, RN
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (01) : 317 - 322
[27] SYNTHESIS OF HETEROCYCLIC-COMPOUNDS USING 1,3-OXATHIOLIUM CATIONS - SYNTHESIS OF THIENO[3,2-E] [1,4]DIAZEPINE, THIAZOLO[4,5-E] [1,4]DIAZEPINE, AND S-TRIAZOLO[3,4-C]THIAZOLO[4,5-E] [1,4]DIAZEPINE DERIVATIVES
HIRAI, K
SUGIMOTO, H
ISHIBA, T
HETEROCYCLES, 1979, 12 (01) : 212 - 212
[28] Synthesis of new heteroaromatic nitrogen ligands:: Pyrimido-[4",5":4′,5′]-thieno[3′,2′:4,5]thieno[3,2-d]pyrimidines and 1,2,3-triazine[4",5":4′,5′]thieno[3′,2′:4,5]thieno[3,2-d]-1,2,3-triazines
Blanco, Gerardo
Quintela, Jose M.
Peinador, Carlos
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (04) : 1051 - 1056
[29] Synthesis and structural studies of a novel scaffold for drug discovery:: a 4,5-dihydro-3H-spirol[1,5-benzoxazepine-2,4′-piperidine]
Willand, N
Beghyn, T
Nowogrocki, G
Gesquiere, JC
Deprez, B
TETRAHEDRON LETTERS, 2004, 45 (05) : 1051 - 1054
[30] SYNTHESIS OF A 1,3,4,5-TETRAHYDROPYRROLO[4,3,2-DE]QUINOLINE FROM A QUINOLINE
VENEMALM, L
ESTEVES, C
ALVAREZ, M
JOULE, JA
TETRAHEDRON LETTERS, 1993, 34 (34) : 5495 - 5496

← 1 2 3 4 5 →