Carbonyl and thiocarbonyl compounds. XIX. Intramolecular cyclization of (2-nitroetheny1)aryl N-arylcarbamates : synthesis of newer series of 3,4-dihydro-2H-1,3-oxazin-2-ones and their antimicrobial activities

Abstract

The hitherto unknown 2-(2-nitroethenyl)aryl and 1-(2-nitroethenyl)naphthalen-2-yl N-arylcarbamates (2) and (5) are readily obtained through the uncatalysed interaction of aryl isocyanates with the corresponding 2-nitroethenyl phenols (1) and (4). The carbamates (2) and (5) cyclize readily at ambient temperature under base catalysis to the corresponding 3-aryl-4-nitromethyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones (3) and 2-aryl-1-nitromethyl-2,3-dihydro-1H-naphth[l,2-e][1,3]oxazin-3-ones (6). The oxazinones (3) are cleaved by hot pyridine affording the corresponding 2-(2-nitroethenyl)phenols and N,N'-diarylurea, whereas, with butylamine, the corresponding aryl(butyl)urea and salicylaldehyde are obtained. The antimicrobial properties of the carbamates and benzoxazinones are evaluated.

Tetramethylammonium hydroxide (TMAH) as an efficient catalyst for the one-pot synthesis of 1,2-dihydro-1-aryl- naphtho[1,2-e][1,3]oxazine-3-ones under solvent-free conditions

“…For example, Latif and his co-workers synthesized 3,4-dihydro-2H-1,3-oxazin-2-ones by intramolecular cyclization of (2-nitroetheny1)aryl N-arylcarbamates and investigated their antimicrobial activities [8]. Also, Wang used this class of compounds as precursors in the preparation of chiral amino phosphine ligands for application in asymmetric catalysis [9].…”

“…Also, Wang used this class of compounds as precursors in the preparation of chiral amino phosphine ligands for application in asymmetric catalysis [9]. However, to the best of our knowledge, only few reports exist on the synthesis of naphthalene-condensed oxazinone derivatives in the literature [8][9][10][11]. Recently, some derivatives of naphthalene-condensed 1,3-oxazin-3-ones were synthesized using condensation of amino alkylnaphthols in the presence of triethylamine [12].…”

Synthesis and Antimicrobial Study of New 8-bromo-1,3-diaryl-2,3-dihydro-1H-naphtho[1,2e][1,3]oxazines

“…1,3-Oxazine derivatives are also known as progesterone receptor agonists (Zhang et al, 2003). Oxazine derivatives have shown analgesic, antipyretic anticonvulsant and antimicrobial activity (Clauson-Kaas et al, 1968;Singh et al, 1995;Latif et al, 1982). Oxazine with naphthalene ring, called naphthoxazine are used in the treatment of Parkinson's disease (Millan et al, 2004;Joyce et al, 2003).…”

An efficient one‐pot synthesis of naphthoxazinones by a three‐component coupling of naphthol, aldehydes, and urea catalyzed by zinc triflate

“…Aromatic-condensed oxazinone derivatives are of significant importance because of their promising biological activities [1]. In addition, these heterocyclic compounds represent an important class of functionalized building blocks.…”

“…The general method for the preparation of 2-aminomethyl phenol derivatives is via the Mannich-type reaction [3]. To the best of our knowledge, there is only one report for the synthesis of 4-aryl-3,4-dihydronaphtho [2,1-e] [1,3]oxazin-2-one derivatives in the literature [4]. However, only few methods are available for the preparation of 1-aryl-1,2-dihydronaphtho[1,2-e] [1,3]oxazin-3-one derivatives [1,4,5].…”