The Pschorr cyclization. A novel Pschorr reaction with a pyrrole derivative: synthesis of a pyrrolo[1,2-c]quinazoline and a new route to arylpyrroles

1970 ◽  
Vol 23 (4) ◽  
pp. 781 ◽  
Author(s):  
S Beveridge ◽  
JL Huppatz

The copper-catalysed decomposition of the diazonium chloride derived from N-(3,5 -diethoxycarbonyl -4-methylpyrrol-2-ylmethyl)-N-methanesulphonyl-o-phenylenediamine (2) gave spiro[l-methanesulphonyl - 3H-indoline - 3,2'- (3', 5'- di-ethoxycarbonyl-4-methyl-2'H-pyrrole)] (4), in high yield. However, thermal decomposition of the diazonium chloride gave 2,4-diethoxy-carbonyl-5-(N-methanesulphonyl-o-aminophenyl)-3-methylpyrrole (3) as the major product. The spiro compound (4) afforded the phenylpyrrole (3) in almost quantitative yield on treatment with concentrated hydrochloric acid, while 100% phosphoric acid or 60% sulphuric acid converted the spiro compound (4) into 1,3-diethoxycarbonyl-5-methanesulphonyl-2-methyl-4,5-dihydropyrrolo[1,2-c]quinazoline (12). The latter reaction could also be achieved thermally. Analytical and spectral data are presented which support the structures proposed.

1962 ◽  
Vol 15 (3) ◽  
pp. 526 ◽  
Author(s):  
RH Hackman

Chitin undergoes rapid and extensive degradation at 20�C when dissolved in ION hydrochloric acid, 21N sulphuric acid, or 85% phosphoric acid. Most of the degradation occurs in the first few minutes after the chitin is dissolved and the products formed are oligosaccharides (which are to some extent deacetylated) and N�acetyl-D.glucosamine. Glucosamine was not found except possibly in the smallest traces. "Colloidal" chitin, prepared by precipitation of chitin from solution in cold 21N sulphuric acid, has a very much shorter chain length than the chitin from which it was prepared. Chitin is more stable in dilute (2N) hydrochloric acid.


1969 ◽  
Vol 22 (9) ◽  
pp. 1975 ◽  
Author(s):  
RC Cambie ◽  
DR Crump ◽  
RN Duve

Attempts have been made to effect fragmentation reactions with bromo- tetralone systems related to 6α-bromo-13-hydroxytotara-8,11,13-trien-7- one (VII), a compound which affords a secoditerpenoid (IX) when treated with DMSO-NaHCO3. On treatment with sulphuric acid in acetone, the mono- epoxide derivative (XXVIII) of the methyl ether of the secoditerpenoid undergoes a novel aromatization to a naphthalenic aldehyde (XXXI) by successive transannular cyclization and fragmentation reactions. ��� A 7β-hydroxy configuration has been confirmed for the major product from reduction of 13-acetoxytotara-8,11,13-trien-7-one (VIII) with lithium aluminium hydride. 13-Methoxytotara-8,11,13-triene (II) has been deisopropylated and then subjected to Birch reduction in an attempt to effect a high yield conversion into (+)-podocarp-8(14)-en- 13-one (XXXVII), a potentially useful intermediate for synthesis.


Molbank ◽  
10.3390/m1187 ◽  
2021 ◽  
Vol 2021 (1) ◽  
pp. M1187
Author(s):  
Stanimir Manolov ◽  
Iliyan Ivanov ◽  
Dimitar Bojilov

The title compound was obtained in high yield in the reaction between tryptamine and naproxen. The newly synthesized naproxen derivative was fully analyzed and characterized via 1H, 13C-NMR, UV, IR, and mass spectral data.


2014 ◽  
Vol 983 ◽  
pp. 190-193
Author(s):  
Cai Yun Sun ◽  
Yong Li Yang ◽  
Ming Gao

Wood has been treated with amino resins and amino resins modified with phosphoric acid to impart flame retardancy. The thermal degradation of samples has been studied by thermogravimetry (TG) in air. From the resulting data, kinetic parameters for different stages of thermal degradation are obtained following the method of Broido. For the decomposition of wood and flame retardant wood, the activation energy is found to decrease from 122 to 72 kJmol-1.


1994 ◽  
Vol 21 (7) ◽  
pp. 565-568 ◽  
Author(s):  
John C. Moore ◽  
Eric W. Wolff ◽  
Henrik B. Clausen ◽  
Claus U. Hammer ◽  
Michel R. Legrand ◽  
...  

1970 ◽  
Vol 48 (22) ◽  
pp. 3554-3562 ◽  
Author(s):  
Mrs. A. L. Lee ◽  
Donald Mackay ◽  
E. L. Manery

2-Thiazolylhydrazine and all three thiazole carbonyl peroxides have been synthesized and examined as radical precursors in solution in benzene, bromobenzene, and cumene. Silver oxide oxidation of the hydrazine or thermal decomposition of the 2-peroxide gives good yields of 2-arylthiazoles but negligible amounts of esters; in cumene a trace of bicumyl is formed. The isomer ratios in bromobenzene and cumene fully support the involvement of 2-thiazolyl radicals (1).The 4-carbonyl peroxide gives fair yields of 4-arylthiazoles but the phenyl ester is also a major product in benzene, indicative of reactions of both 4-thiazolyl radicals (2) and thiazole-4-carbonyloxy radicals. The 5-peroxide gives no products clearly diagnostic of 5-thiazolyl radicals (3) or thiazole-5-carbonyloxy radicals. Bicumyl is a major product of the reactions of the 4- and the 5-peroxides in cumene.


2019 ◽  
Vol 131 ◽  
pp. 404-409 ◽  
Author(s):  
Weiqing Li ◽  
Ruichao Peng ◽  
Peng Ye ◽  
Xianhe lv ◽  
Tianrong Zhu ◽  
...  

Author(s):  
Konstantin G. Gorbovskiy ◽  
Alena S. Ryzhova ◽  
Andrey M. Norov ◽  
Denis A. Pagaleshkin ◽  
Valentina N. Kalinina ◽  
...  

Complex mineral ammonium nitrate-based fertilizers are complex multicomponent salt systems possessing low thermal stability and prone to self-sustaining decomposition. This leads to the need to increase the requirements for fire and explosion safety in their manufacture, storage and transportation, caused by the fact that ammonium nitrate is a solid oxidant able to support a combustion, and its heating in confined space can lead to detonation. Components that make up such fertilizers can both reduce (phosphates and ammonium sulfate) and accelerate (chlorine compounds) decomposition of ammonium nitrate. Thus, the thermal stability of fertilizers based on ammonium nitrate largely depends on the ratio of the components that make up its composition or formed as a result of the chemical reaction. The simplest way to reduce the content of ammonium nitrate and increase the thermal stability of fertilizer without changing the content of essential nutrients is to increase the degree of phosphoric acid ammoniation. In this paper, the phase composition change of grade 22:11:11 nitrogen-phosphorus-potassium fertilizer obtained with different ammoniation degree in the process of thermal decomposition was studied by X-ray phase analysis. To obtain this fertilizer, wet-process phosphoric acid obtained sulfuric acid attack of the Khibin apatite concentrate by a hemihydrate method is used. It is shown that an increase in the ammoniation degree has a significant effect on the exothermic decomposition of ammonium nitrate and the amount of material that is released into the gas phase. The phases formed at each stage of the decomposition are determined.Forcitation:Gorbovskiy K.G., Ryzhova A.S., Norov A.M., Pagaleshkin D.A., Kalinina V.N., Mikhaylichenko A.I. Study of thermal decomposition products of nitrogen-phosphorus-potassium fertilizers based on ammonium nitrate by X-ray diffractuon. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2018. V. 61. N 1. P. 72-77


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