Gas-phase thermolysis of 1-acylnaphtho[1,8-de][1,2,3]triazines.: Interesting direct routes towards condensed naphtho[1,8-de] heterocyclic ring systems

被引：16

作者：

Al-Awadi, H ^{[1
]}

Ibrahim, MR ^{[1
]}

Dib, HH ^{[1
]}

Al-Awadi, NA ^{[1
]}

Ibrahim, YA ^{[1
]}

机构：

[1] Kuwait Univ, Fac Sci, Dept Chem, Kuwait 13060, Kuwait

来源：

TETRAHEDRON | 2005年 / 61卷 / 44期

关键词：

FVP; naphtho[1,8-de][1,2,3]triazines; naphtho[1,8-de][1,3]oxazines; heterocycles;

D O I：

10.1016/j.tet.2005.08.047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

FVP pyrolysis of 1-acylnaphtho[1,8-de][1,2,3]triazines at 500 degrees C and 10(-2) Torr gave exclusively the corresponding 2-substituted naphtho[1,8-de][1,3]oxazines. The latter was also obtained by static pyrolysis but in lower yield along with the corresponding N-(naphthalen-l-yl)acylamides. The reaction was studied kinetically and mechanistically. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：10507 / 10513

页数：7

共 38 条

[1] Gas-phase thermolysis of benzotriazole derivatives. Part 3: Kinetic and mechanistic evidence for biradical intermediates in pyrolysis of aroylbenzotriazoles and related compounds
Al-Awadi, NA
George, BJ
Dib, HH
Ibrahim, MR
Ibrahim, YA
El-Dusouqui, OME
[J]. TETRAHEDRON, 2005, 61 (34) : 8257 - 8263
[2] Gas-phase pyrolysis of thiopheneacetic acids, thienylethanols, and related compounds -: protophilicity of ring π-electrons and relative acidities of hydrogen-bond donors of hydroxyl groups
Al-Juwaiser, IA
Al-Awadi, NA
El-Dusouqui, OME
[J]. CANADIAN JOURNAL OF CHEMISTRY, 2002, 80 (05) : 499 - 503
[3] A comparison of the flash vacuum pyrolysis products of some N-acylbenzotriazoles and N-acylbenzisoxazolones
Baradarani, MM
Khalafy, J
Prager, RH
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (08) : 775 - 780
[4] FLASH-PYROLYSIS OF 1-VINYLBENZOTRIAZOLES
BARKER, SJ
STORR, RC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03): : 485 - 488
[5] FLASH VACUUM PYROLYSIS OF 1-ALLYLBENZOTRIAZOLES AND DIHYDROBENZOXAZINES - FORMATION OF QUINOLINES
BARKER, SJ
JONES, GB
RANDLES, KR
STORR, RC
[J]. TETRAHEDRON LETTERS, 1988, 29 (08) : 953 - 954
[6] Flash vacuum pyrolysis of N-alkenylbenzotriazoles and N-alkenylisoxazolones
Cox, M
Heidarizadeh, F
Prager, RH
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (08) : 665 - 671
[7] Gas-phase thermolysis of benzotriazole derivatives:: part 1 -: synthesis of α-N(1)- and N(2)-benzotriazolyl ketones and kinetics and mechanism of their gas-phase pyrolysis
Dib, HH
Al-Awadi, NA
Ibrahim, YA
El-Dusouqui, OME
[J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2004, 17 (04) : 267 - 272
[8] Gas-phase thermolysis of benzotriazole derivatives.: Part 2:: Synthesis of benzimidazo[1,2-b]cinnolines, a novel heterocyclic ring system, by pyrolysis of benzotriazole derivatives.: Kinetic and mechanistic study
Dib, HH
Al-Awadi, NA
Ibrahim, YA
El-Dusouqui, OME
[J]. TETRAHEDRON, 2003, 59 (47) : 9455 - 9464
[9] RATE PH PROFILE FOR THE FORMATION OF 1-HYDROXY-8-ACETYLAMINONAPHTHALENE FROM 2-METHYLNAPHTH[1,8-DE]-1.3-OXAZINE IN AQUEOUS-SOLUTION - ACID CATALYSIS AND INHIBITION AND COMPARISON WITH THE REACTION OF 1-AMINO-8-TRIFLUOROACETYLAMINONAPHTHALENE
DIXON, WJ
HIBBERT, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (04): : 795 - 798
[10] THERMAL INTERMOLECULAR EXCHANGE BETWEEN N-ACYLBENZOTRIAZOLES
DRULINER, JD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (24) : 6879 - &

← 1 2 3 4 →