An Efficient Scalable Synthesis of 2,3-Epoxypropyl Phenylhydrazones

Abstract

A series of mono and di-N-2,3-epoxypropyl N-phenylhydrazones have been prepared on a large scale by reaction of the corresponding N-phenylhydrazones of 9-ethyl-3-carbazolecarbaldehyde, 9-ethyl-3,6-carbazoledicarbaldehyde, 4-dimethylamino-, 4-diethylamino-, 4-benzylethylamino-, 4-(diphenylamino)-, 4-(4,4‫-ۥ‬dimethyl-diphenylamino)-, 4-(4-formyldiphenylamino)-and 4-(4-formyl-4‫-ۥ‬methyldiphenyl-amino)benzaldehyde with epichlorohydrin in the presence of KOH and anhydrous Na 2 SO 4 .

“Click-chemistry” inspired synthesis of hydrazone-based molecular glasses

“…Thus formed anions immediately reacted with appropriate halogen compound (1,3-bis(bromomethyl)benzene or 1,2,4,5tetrakis(bromomethyl)benzene) in a nucleophilic substitution to give twin molecules 2Ha and 2Hb, or tetramers 4Ha and 4Hb, possessing photoconductive hydrazone moieties. Starting precursors Ha and Hb were freshly prepared by a simple reaction of corresponding aromatic aldehyde with phenylhydrazine 15 and were directly used for the subsequent synthesis just aer ltration and washing with hexane. In all cases, the processes proceeded rapidly and the twins 2Ha, 2Hb, as well as the tetrahydrazones 4Ha, 4Hb crystallized during the reaction.…”

“…However, they have two main disadvantages: complicated synthesis process with low yields 14 and high environmental impact. 15,16 In the beginning of the 21 st century, novel trend appeared in the synthetic chemistry called "click chemistry". 17 The main idea is to adopt simple reactions for fast and versatile search of novel materials.…”

Organic Dyes with Hydrazone Moieties: A Study of Correlation between Structure and Performance in the Solid-State Dye-Sensitized Solar Cells

“…Chemicals were purchased from Aldrich and TCI Europe and used as received without further purification. 4-(N-(4-Methylphenyl)-Nphenylamino)benzaldehyde (1b), 35 36 and {5-[4-(diphenylamino)benzylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}acetic acid (TPA-R) 37 were synthesized according to the earlier reported procedures. 4-(N,N-Diphenylamino)benzaldehyde (1a) was purchased from TCI Europe.…”

“…Chemicals were purchased from Aldrich and TCI Europe and used as received without further purification. 4-( N -(4-Methylphenyl)- N -phenylamino)benzaldehyde ( 1b ), N , N -diphenyl-4-[(2-phenylhydrazinylidene)methyl]aniline ( 2a ), 4-methyl- N -phenyl- N -{4-[(2-phenylhydrazinylidene)methyl]phenyl}aniline ( 2b ), 4,4′-(phenylimino)dibenzaldehyde ( 6a ), 4,4′-[(4-methylphenyl)imino]dibenzaldehyde ( 6b ), and {5-[4-(diphenylamino)benzylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}acetic acid ( TPA-R ) were synthesized according to the earlier reported procedures. 4-( N,N -Diphenylamino)benzaldehyde ( 1a ) was purchased from TCI Europe.…”