A CONVENIENT SYNTHETIC METHOD FOR FLUORINE-CONTAINING 4-ALKOXYDIHYDROBENZO[b][1,4]DIAZEPINOLS AND 3H-BENZO[b][1,4]DIAZEPINES BY THE REACTION OF β-TRIFLUOROACETYLKETENE ACETALS WITH 1,2-PHENYLENEDIAMINES

被引：7

作者：

Ota, Norio ^{[1
]}

Okada, Etsuji ^{[1
]}

Terai, Naoya ^{[1
]}

Miyamura, Tomomi ^{[1
]}

Shibata, Dai ^{[1
]}

Sakata, Tsuneaki ^{[2
]}

机构：

[1] Kobe Univ, Dept Sci & Chem Engn, Grad Sch Engn, Nada Ku, Kobe, Hyogo 6578501, Japan

[2] Kobe Univ, Dept Life Sci, Grad Sch Sci & Technol, Nada Ku, Kobe, Hyogo 6578501, Japan

来源：

HETEROCYCLES | 2009年 / 77卷 / 02期

关键词：

2,3-Dihydro-1H-benzo[b][1,4]diazepinol; 3H-Benzo[b][1,4]diazepine; Trifluoromethyl Group; Annulation; 1,2-Phenylenediamine; FACILE SYNTHESES; OXAZOLES;

D O I：

10.3987/COM-08-S(F)72

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Trifluoroacetylketene dialkyl acetals (3 and 5) reacted easily with various 1,2-phenylenediamines to give novel 4-alkoxy-2-trifluoromethyl-2,3-dihydro-1H-benzo[b][1,4]diazepinols (6 and 8) in moderate to high yields. Dehydration of 6 and 8 proceeded thermally under reduced pressure to afford the corresponding fluorine-containing 3H-benzo[b][1,4]diazepines (7 and 9).

引用

页码：983 / 990

页数：8

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] A VERSATILE AND CONVENIENT METHOD FOR THE SYNTHESIS OF PYRIMIDO[4,5-B] [1,4]THIAZINES
SAKO, M
NIWA, T
HIROTA, K
MAKI, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1984, 32 (06) : 2474 - 2476
[23] First Synthesis of 4H-Furo[3,2-f]pyrrolo[1,2-a] [1,4]diazepines
Feng, X.
Lancelot, J.-C.
Prunier, H.
Rault, S.
Journal of Heterocyclic Chemistry, 1996, 33 (06)
[24] An Efficient Synthetic Approach Towards Benzo[b]pyrano[2,3-e][1,4]diazepines, and Their Cytotoxic Activity
El Azab, Islam H.
Elkanzi, Nadia A. A.
MOLECULES, 2020, 25 (09):
[25] SYNTHETIC APPLICATION OF LITHIATION REACTIONS .10. SYNTHESIS OF DIBENZO[B,F][1,4]OXAZEPINE, DIBENZO[B,F][1,4]THIAZEPINE, AND 5H-DIBENZO[B,E][1,4]-DIAZEPINE
NARASIMHAN, NS
CHANDRACHOOD, PS
SYNTHESIS-STUTTGART, 1979, (08): : 589 - 590
[26] Synthesis of 1,4-Diazepanes and Benzo[b][1,4]diazepines by a Domino Process Involving the In Situ Generation of an Aza-Nazarov Reagent
Maiti, Swarupananda
Leonardi, Marco
Cores, Angel
Tenti, Giammarco
Ramos, M. Teresa
Villacampa, Mercedes
Carlos Menendez, J.
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (18): : 11924 - 11933
[27] A new and convenient synthetic method for 1,2,3,5,6,11b-hexahydroimidazo[1,2-d][1,4]benzoxazepine and its derivatives
Mizyed, Shehadeh A.
Ashram, Muhammad
Awwadi, Firas F.
ARKIVOC, 2011, : 277 - 286
[28] STUDY OF SYNTHETIC APPROACHES TO 4 H-5,6 DIHYDROPYRROLO [1,2-ALPHA] THIENO [3,2-F]-1,4 DIAZEPINES
RAULT, S
CUGNONDESEVRICOURT, M
ROBBA, M
COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1977, 285 (11): : 381 - 383
[29] PYRIDAZINE DERIVATIVES .10. 10H-BENZO[B]PYRIDAZINO[3,4-E][1,4]THIAZINE AND 5H-BENZO[B]PYRIDAZINO[4,3-E][1,4]THIAZINE
YONEDA, F
OHTAKA, T
NITTA, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1966, 14 (07) : 698 - +
[30] First synthesis of 4H-furo[3,2-f]pyrrolo[1,2-alpha][1,4]diazepines
Feng, X
Lancelot, JC
Prunier, H
Rault, S
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (06) : 2007 - 2011

← 1 2 3 4 5 →