Reactions of 2-aza-21-carbaporphyrin with aniline derivatives

Abstract

Post-synthetic modification of N-confused porphyrin (NCP) yields chiral 21-arylazo- or 3,21-bis(arylamino)-NCP in one-step, one-pot reactions of NCP with anilines.

Creation from Confusion and Fusion in the Porphyrin World─The Last Three Decades of N-Confused Porphyrinoid Chemistry

“…In 157, the N-confused pyrrole ring was tilted significantly to avoid 209,210 Later, direct synthesis of 21-azo-NCP was reported by the reactions of NCP with aniline derivative and isoamyl nitrite. 191 When 120 was treated with mesitylaldehyde 36d, 21-imino-NCTPP 164 was obtained in 28% yield (Scheme 58). 188 Interestingly, when less-hindered benzaldehyde 36b was used in place of mesitylaldehyde, bridged NCP 167 in 47−53% yields (Scheme 59).…”

“…The reaction of 21-amino-NCTPP 120 with nitrosobenzene gave 21-azoky-NCTPP 162 in 71% yield (Scheme ). The reduction of 162 by the rhenium-catalyzed oxygen atom transfer reaction afforded 21-azo-NCTPP 163 in 35% yield. , Later, direct synthesis of 21-azo-NCP was reported by the reactions of NCP with aniline derivative and isoamyl nitrite . When 120 was treated with mesitylaldehyde 36d , 21-imino-NCTPP 164 was obtained in 28% yield (Scheme ).…”

“…derivatives in the presence of DDQ, diamination reactions proceeded to give 3,21-diaminated NCP 125 in 50−67% yields (Scheme 43) 191. 3.3.5.…”

Clean Preparation of Quinolin-2-yl Substituted Ureas in Water

“…According to previous reports, the C2 position of quinoline N -oxides may be functionalized via a number of reaction processes, which include the C–H bond alkylation, − arylation, alkenylation, − acetoxylation, , sulfonylation, − amidation, − amination, − hydroxylation, , phosphonation, , and thiolation of quinoline N -oxides. However, to the best of our knowledge, the preparation of quinolin-2-yl substituted ureas from readily available quinoline N -oxides has never been reported.…”

Practical Approach for Clean Preparation of Z-β-Thiocyanate Alkenyl Esters

“…β-Thiocyanate alkenyl esters represent highly valuable multifunctional compounds because both alkenyl ester − and alkenyl thiocyanate − moieties are broadly utilized in various fields such as organic synthesis, pharmacy, and material science. Directly converting propargylic carboxylates into β-thiocyanate alkenyl esters through multicomponent reaction − represents a highly attractive transformation in organic synthesis, given the easily available raw materials.…”