New 1,3,5-heterocyclohexanes:: Dioxazines, oxadiazines, thiadiazines, oxathiazines and triazines and their amination, transamination and disproportionation reactions

被引：22

作者：

Flores-Parra, A ^{[1
]}

Sánchez-Ruíz, SA ^{[1
]}

机构：

[1] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Chem, Mexico City 07000, DF, Mexico

来源：

HETEROCYCLES | 1999年 / 51卷 / 09期

关键词：

D O I：

10.3987/COM-99-8583

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New 1,3,5-heterocyclohexanes: 5-alkyl-1,3,5-dioxazines (R= iPr, tBu and [R]-alpha-methylbenzyl), 3,5-di([R]-alpha-methylbenzyl)-1,3,5-oxadiazine, 3,5-di([R]-alpha-methylbenzyl)-1,3,5-thiadiazine. 5-isopropyl-1,3,5-oxathiazine, 1-isopropyl-3,5-dimethyl-1,3,5-triazine, 1-tert-butyl-3,5-dimethyl-1,3,5-triazine are reported. Amination and transamination reactions of 1,3,5-heterocyclohexanes were investigated. Equilibria between different heterocycles were found. C-13 NMR studies allowed to observe new 1,3,5-heterocycles: 1,3,5-triazines bearing two different alkyl substituents, 3,5-ditert-butyl-1,3,5-thiadiazine, 3-tert-butyl-5-isopropyl-1,3,5-oxadiazine. 1,3,5-heterocyclohexanes present a ring fluxional behavior, the ring inversion energy was calculated for dioxazines, oxadiazine, thiadiazines and triazines.

引用

页码：2079 / 2092

页数：14

共 22 条

[1] CONFORMATIONAL-ANALYSIS OF SATURATED HETEROCYCLES .45. ALKYLDIHYDRO-1,3,5-DITHIAZINES AND ALKYLTETRAHYDRO-1,3,5-THIADIAZINES [J].

ANGIOLINI, L ;

KATRIZKY, AR ;

JONES, RAY ;

DUKE, RP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (05) :674-+

[2] CONFORMATIONAL-ANALYSIS OF SATURATED HETEROCYCLES .84. CONFORMATIONAL CONSEQUENCES OF INTERNAL BETA-HETEROATOMS - RING AND NITROGEN INVERSION IN 3,5-DIMETHYL-1-OXA-3,5-DIAZA-CYCLOHEXANES, 5-METHYL-1,3-DIOXA-5-AZA-CYCLOHEXANES AND 1,3,5-TRIMETHYL-1,3,5-TRIAZA-CYCLOHEXANES 1,3,5-TRIETHYL-1,3,5-TRIAZA-CYCLOHEXANES 1,3,5-TRI-ISOPROPYL-1,3,5-TRIAZA-CYCLOHEXANES AND 1,3,5-TRI-T-BUTYL-T-1,3,5-TRIAZA-CYCLOHEXANESR [J].

BAKER, VJ ;

FERGUSON, IJ ;

KATRITZKY, AR ;

PATEL, R ;

RAHIMIRASTGOO, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (04) :377-381

[3] THE ACTION OF HYDROGEN SULPHIDE ON CERTAIN METHYLENEIMINES .2. [J].

BRAITHWAITE, ER ;

GRAYMORE, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1953, (JAN) :143-145

[4] THE ACTION OF HYDROGEN SULPHIDE ON CERTAIN METHYLENEIMINES .1. [J].

BRAITHWAITE, ER ;

GRAYMORE, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1950, (JAN) :208-210

[5] NEW CHIRAL HETEROCYCLES - 5-[(R)-(+)-1'-METHYLBENZYL]-1,3,5-DITHIAZINE AND 3,7-DI-[(R)-(+)-1'-METHYLBENZYL]-3,7-DIAZA-1,5-DITHIACYCLOOCTANE - CONFORMATIONAL STUDIES AND THEIR REACTIONS WITH BORANE [J].

CADENASPLIEGO, G ;

ROSALESHOZ, MD ;

CONTRERAS, R ;

FLORESPARRA, A .

TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :633-640

[6] NEW PERHYDRODITHIAZINES, NMR AND X-RAY-DIFFRACTION STUDIES [J].

CADENASPLIEGO, G ;

MARTINEZAGUILERA, LMR ;

BELLORAMIREZ, AM ;

ROSALESHOZ, MD ;

CONTRERAS, R ;

DARAN, JC ;

HALUT, S ;

FLORESPARRA, A .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 81 (1-4) :111-123

[7]

CARDENASPLIEGO G, 1993, PHOSPHORUS SULFUR, V84, P9

[8] CONFORMATIONAL ISOMERIZATION IN HEXAHYDRO-S-TRIAZINES AND HEXAHYDROPYRIMIDINES [J].

FARMER, RF ;

HAMER, J .

TETRAHEDRON, 1968, 24 (02) :829-&

[9] NMR-STUDY OF THE EFFECT OF NITROGEN-BORANE COORDINATION ON THE CONFORMATIONAL EQUILIBRIUM OF 6 MEMBERED RING HETEROCYCLES [J].

FLORESPARRA, A ;

FARFAN, N ;

HERNANDEZBAUTISTA, AI ;

FERNANDEZSANCHEZ, L ;

CONTRERAS, R .

TETRAHEDRON, 1991, 47 (34) :6903-6914

[10] REACTIVITY OF DIATHIAZINANES TOWARDS BH3, BD3 AND BF3 - NEW HETEROCYCLES - 5,5-DIMETHYL-1,3-DITHIA-5-AZONIA-4-BORATACYCLOHEXANE AND 6,6-DIDEUTERIO-5-METHYL-5-[D(1)]METHYL-1,3-DITHIA-5-AZONIA-4-BORATACYCLOHEXANE - A METHOD FOR THE DIMETHYLATION AND MONODEUTERIOMETHYLATION OF PRIMARY AMINES [J].

FLORESPARRA, A ;

CADENASPLIEGO, G ;

MARTINEZAGUILERA, LMR ;

GARCIANARES, ML ;

CONTRERAS, R .

CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (04) :863-867

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