85285-38-7

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 109-73-9 N-butylamine 
• 14210-25-4 5-Chloro-1-phenyltetrazole 
• 6336-01-2 3-n-butyl-1-phenylthiourea 
• 21848-95-3 N-phenyl-N'-(n-butyl)carbodiimide 

Relevant academic research and scientific papers

Solid-phase synthesis of 5-aminotetrazoles

A solid-phase synthesis of 5-aminotetrazoles is described. Resin-bound thioureas were displaced by sodium azide in the presence of HgCl2 and following nucleophilic cyclization produced the resin-bound products. The desired 5-aminotetrazoles were cleaved from the resin using 95% trifluoroacetic acid in dichloromethane in good yield and purity.

Method for preparing 5-aminotetrazole compound

The invention discloses a method for preparing a 5-aminotetrazole compound. The method comprises the following steps: adding bis-substituted selenourea shown in the formula II in the description, ionic liquid loaded iodobenzene diacetate shown in the formula III in the description, sodium azide and alkali A into a solvent B, stirring at -10 to -80 DEG C and conducting cyclization reaction, and after the reaction is finished, conducting aftertreatment on the reaction liquid to prepare the 5-aminotetrazole compound shown in the formula I in the description. Compared with the conventional method, a green reagent, namely, ionic liquid loaded iodobenzene diacetate, is adopted, so that the use of heavy metal is avoided, the operation is simple and convenient, and the reaction yield is high.

An expedient route to the azoles through oxidative desulfurization using iodine reagent

A novel and expedient regioselective method for the synthesis of 5-aminotetrazoles and 3-amino-1,2,4-triazoles through oxidative desulfurization of corresponding 1,3-disubstituted thioureas has been discovered and optimized for the process conditions. The process is broadly applicable to structurally diverse 1,3-disubstituted thioureas.

O -iodoxybenzoic acid mediated oxidative desulfurization initiated domino reactions for synthesis of azoles

A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.

Inhibitors of protein isoprenyl transferases

Compounds having the formula or a pharmaceutically acceptable salt thereof wherein R1is (a) hydrogen, (b) loweralkyl, (c) alkenyl, (d) alkoxy, (e) thioalkoxy, (f) halo, (g) haloalkyl, (h) aryl-L2—, and (i) heterocyclic-L2—; R2is selected from (a) (b) —C(O)NH—CH(R14)—C(O)OR15, (d) —C(O)NH—CH(R14)—C(O)NHSO2R16, (e) —C(O)NH—CH(R14)-tetrazolyl, (f) —C(O)NH-heterocyclic, and (g) —C(O)NH—CH(R14)—C(O)NR17R18; R3is substituted or unsubstituted heterocyclic or aryl, substituted or unsubstituted cycloalkyl or cycloalkenyl, and —P(W)RR3RR3′; R4is hydrogen, lower alkyl, haloalkyl, halogen, aryl, arylakyl, heterocyclic, or (heterocyclic)alkyl; L1is absent or is selected from (a) —L4—N(R5)—L5—, (b) —L4—O—L5—, (c) —L4—S(O)n—L5— (d) —L4—L6—C(W)—N(R5)—L5—, (e) —L4—L6—S(O)m—N(R5)—L5—, (f) —L4—N(R5)—C(W)—L7—L5—, (g) —L4—N(R5)—S(O)p—L7—L5—, (h) optionally substituted alkylene, (i) optionally substituted alkenylene, (j) optionally substituted alkynylene (k) a covalent bond, (l) and (m) are inhibitors of protein isoprenyl transferases. Also disclosed are protein isoprenyl transferase inhibiting compositions and a method of inhibiting protein isoprenyl transferases.

Reactions of Trimethylsilyl Azide with Heterocumulenes

Trimethylsilyl azide (TMSA) reacted with aryl isocyanates to give arylcarbamoyl azides, 1-aryl-5(4H)-tetrazolinones, and / or 1-aryl-4-(arylcarbamoyl)-5(4H)-tetrazolinones, whose yields were dependent on the reaction conditions.The reaction between TMSA and benzoyl or thiobenzoyl isocyanates provides a facile method for the preparation of 5-aryl-3-hydroxy-1,2,4-oxadiazoles or -1,2,4-thiadiazoles, respectively.However, with phenyl or benzoyl isothiocyanate, 1-anilino-1,2,3,4-thiatriazole or benzoylcyanamide was obtained in low yield, respectively.TMSA reacted with carbodiimides to afford the corresponding 5-aminotetrazoles.Tetraphenylsuccinimide, N-(diphenylacetyl)tetraphenylsuccinimide, 1,3-bis(diphenylmethyl)urea, and / or benziloylamide were obtained from the reaction of TMSA with diphenyl ketene.The pathways for the formation of the above products are also described.