An efficient combination of Dess-Martin periodinane with molecular iodine and KBr for the facile oxidative aromatization of Hantzsch 1,4-dihydropyridines

Abstract

A highly efficient, mild, and simple protocol is presented for the oxidative aromatization of Hantzsch 1, 4-dihydropyridines using the combination of Dess-Martin periodinane with molecular iodine or KBr. The in situ generated acetyl hypoiodite or bromite formed due to the reaction between Dess-Martin periodinane and molecular iodine or KBr respectively is supposed to be the responsible species for bringing about the oxidative aromatization of 1, 4-dihydropyridines.

Advances in Synthetic Applications of Hypervalent Iodine Compounds

“…This methodology allows controlled oxidation of pyrroles 578 to give the functionalized γ-lactams 579 in good yields (Scheme ). DMP can be also used for the facile oxidative aromatization of heterocyclic compounds. , …”

“…DMP can be also used for the facile oxidative aromatization of heterocyclic compounds. 1435,1436 Palladium-catalyzed oxidative cycloisomerization of 3-cyclopropylideneprop-2-en-1-ones 580 with DMP 536 has been used for the facile synthesis of a highly strained functionalized 2-alkylidenecyclobutanone 581 (Scheme 169). The obtained cyclobutanone products 581 can be easily converted to furanones with a spiro-cyclopropane unit by treatment with acid.…”

Mild oxidative aromatization of 1,4-dihydropyridines with trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane promoted by ammonium bromide/HOAc in water/MeCN

“…As regards the importance of gem-dihydroperoxides, trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane (DHPDMO) has been synthesized and used as a new, solid, and powerful oxidant in organic synthesis by our research group (Anniyappan et al, 2002;Dehghanpour, Heravi, & Derikvand, 2007;Fang, Liu, & Li, 2007;Filipan-Litvić, Litvić, & Vinkinić, 2008a;Filipan-Litvić, Litvić, & Vinkinić, 2008b;Gorjizadeh & AbdollahiAlibeik, 2011;Heravi, Behbahani, Oskooie, & Shoar, 2005;Heravi et al, 2009;Karade, Gampawar, Kondre, & Shinde, 2008;Ko & Kim, 1999;Mao, Jin, Liu, & Wu, 2000;Mashraqui & Karnik, 1998;Zolfigol et al, 2005;Zeynizadeh, Dilmaghani, & Mirzaei, 2007). DHPDMO is prepared easily from acetyl acetone and aqueous hydrogen peroxide in the presence of silica sulfuric acid (SSA) (Anniyappan et al, 2002) (Scheme 1).…”

Highly Efficient, One Pot Synthesis and Oxidation of Hantsch 1,4-Dihydropyridines Mediated by Iodobenzene Diacetate (III) Using Conventional Heating, Ultrasonic and Microwave Irradiation

“…Newly synthesized substituted 1,4-DHPs possess other pharmacological activities such as antitumor [4], bronchodilating [5], antidiabetic [6], neurotropic [7], antianginal [8] and P-glyco protein Inhibitors [9]. The benign environmental character and easy commercial availability makes hypervalent iodine (III) reagents increasingly important for the oxidation of organic molecules [10]- [18]. These days much work has been done to explore the oxidation ability, their electrophilic properties and to develop novel reaction using hypervalent iodine compounds [19].…”