Stereoselective synthesis of dihydrothiadiazinoazines and dihydrothiadiazinoazoles and their pyrolytic desulfurization ring contraction

被引：23

作者：

Al-Etaibi, Alya ^{[2
]}

John, Elizabeth ^{[1
]}

Ibrahim, Maher R. ^{[1
]}

Al-Awadi, Nouria A. ^{[1
]}

Ibrahim, Yehia A. ^{[1
]}

机构：

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

[2] Publ Author Appl Educ & Training, Coll Hlth Sci, Dept Nat Sci, Kuwait, Kuwait

来源：

TETRAHEDRON | 2011年 / 67卷 / 34期

关键词：

Pyrolysis; Stereoselective synthesis; 1,2,4]Triazolo[3,4-b][1,3,4]thiadiazines; 1,2,4]Triazino[3,4-b][1,3,4]thiadiazin-4-ones; 1,3,4]Thiadiazino[2,3-b]quinazolin-10-ones; Pyrazolo[5,1-b][1,2,4]triazoles; Pyrazolo[5,1-c][1,2,4]triazin-4-ones; Pyrazolo[4,3-b]quinazolin-9-ones; GAS-PHASE THERMOLYSIS; CARBONATE PYROLYSIS; INTERESTING ROUTES; SCHIFF-BASES; CYCLIZATION; SYSTEMS;

D O I：

10.1016/j.tet.2011.06.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular base catalyzed C-C bond formation led to exclusive stereoselective syntheses of trans-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines, trans-7,8-dihydro-6H-[1,2,4]triazino[3,4-b] [1,3,4]thiadiazin-4-ones, and trans-3,4-dihydro-2H-[1,3,4]thiadiazino[2,3-b]quinazolin-10-one. trans-6,7-Dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines isomerize slowly in CDCl(3) and more rapidly in DMSO-d(6) into the corresponding cis-stereoisomers. The other trans-6,7-dihydro-1 1,3,4]thiadiazines isomerize also in DMSO-d6 into the corresponding cis-stereoisomers. Pyrolytic conversion of these heterocyclic condensed dihydrothiadiazines into their corresponding pyrazolo[5,1-b][1,2,4]triazoles, pyrazolo[5,1-c][1,2,4]triazin-4-ones and pyrazolo[4,3-b]quinazolin-9-ones via desulfurization ring contraction is described. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6259 / 6274

页数：16

共 23 条

[1] Gas-phase thermolysis of condensed-1,2,4-triazines: interesting routes toward heterocyclic ring systems [J].

Al-Awadi, Hanan ;

Ibrahim, Maher R. ;

Al-Awadi, Nouria A. ;

Ibrahim, Yehia A. .

TETRAHEDRON, 2007, 63 (52) :12948-12953

[2] GAS-PHASE PYROLYSIS OF DITHIOACETATES - REMARKABLE CONSTANCY OF SUBSTITUENT EFFECTS [J].

ALAWADI, N ;

BIGLEY, DB ;

GABBOTT, RE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (12) :1223-1224

[3] CARBONATE PYROLYSIS .5. GAS-PHASE PYROLYSIS OF SOME UNSYMMETRICAL MONOTHIOLCARBONATES AND A RATIONALIZATION OF THE RATES OF SOME RELATED REACTIONS [J].

ALAWADI, N ;

BIGLEY, DB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (04) :497-500

[4] CARBONATE PYROLYSIS .6. THE KINETICS AND MECHANISM OF THE PYROLYSIS OF THION-CARBONATE AND DITHIO-CARBONATE - IMPLICATIONS FOR THE TRANSITION-STATE IN CARBONATE PYROLYSIS [J].

ALAWADI, N ;

BIGLEY, DB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1982, (07) :773-775

[5] SYNTHESIS AND STRUCTURE OF AS-TRIAZINOQUINAZOLINES .2. [J].

BADAWY, MA ;

ABDELHADY, SAL ;

EID, MM ;

IBRAHIM, YA .

CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (03) :1083-1088

[6]

Bazavova I. M., 2003, CHEM HETEROCYCL COMP, V39, P809

[7] SYNTHESEN STICKSTOFFHALTIGER HETEROCYCLEN .27. UBER 1.2.4-TRIAZINE .1. DARSTELLUNG EINIGER NEUER S-TRIAZOLO(3.2-C)-AS-TRIAZINE [J].

DORNOW, A ;

MENZEL, H ;

MARX, P .

CHEMISCHE BERICHTE-RECUEIL, 1964, 97 (08) :2173-&

[8] Synthesis of some novel 3,7-dimethyl-4H-pyrazolo[5,1-c][1,2,4]triazin-4-ones [J].

El-Barbary, AA ;

El-Badawi, MA ;

Loksha, YM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (03) :711-716

[9] Synthesis of spiro[indole-3,3'-[1,3,4]thiadiazino[3,2-a]benzimidazoles] and spiro[indole-3,6'-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines] [J].

Gaponenko, N. I. ;

Kolodina, A. A. ;

Lesin, A. V. ;

Kurbatov, S. V. ;

Starikova, Z. A. ;

Nelyubina, Yu. V. .

RUSSIAN CHEMICAL BULLETIN, 2010, 59 (04) :838-844

[10]

HAJOS G, 1996, BICYCLIC 5 6 SYSTEMS, V8, P445

← 1 2 3 →