65103-33-5

Upstream product

• 1119-51-3 bromopentene 
• 18039-42-4 5-phenyl-2H-1,2,3,4-tetrazole 
• 18039-42-4 5-Phenyl-1H-tetrazole 
• 7411-18-9 3-methylsulfanyl-4H-[1,2,4]triazole 

Downstream Products

• 65103-38-0 2-phenyl-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazole 

Relevant academic research and scientific papers

5-(Methylthio)tetrazoles as versatile synthons in the stereoselective synthesis of polycyclic pyrazolines via photoinduced intramolecular nitrile imine-alkene 1,3-dipolar cycloaddition

A key thioether substituent in readily accessible 2-alkyl-5-(methylthio) tetrazoles enables facile photoinduced denitrogenation and intramolecular nitrile imine 1,3-dipolar cycloaddition to afford a wide range of polycyclic pyrazoline products with excellent diastereoselectivity. The methylthio group red-shifts the UV absorbance of the tetrazole, obviating the requirement in all previous substrate systems for at least one aryl substituent, and can subsequently be converted into a variety of other functionalities. This synthetic platform has been applied to the concise total syntheses of the alkaloid natural products (±)-newbouldine and withasomnine. This journal is the Partner Organisations 2014.

Intramolecular Photocycloaddition Reactions in the 2-(4-Pentenyl)-5-aryl-Substituted Tetrazole System

Irradiation of 2-(4-pentenyl)-5-aryl-substituted tetrazoles with UV light results in the loss of nitrogen and formation of a nitrile imine intermediate.This reactive 1,3-dipole undergoes an intramolecular 1,3-dipolar cycloaddition reaction to produce a bicyclopyrazoline ring.The primary photochemical process occurs from the n?* excited singlet state.The effect of substituents on the para position of the 5-phenyl group of the tetrazole ring was examined.A kinetic investigation, involving Stern-Volmer plots and relative reactivity studies, shows that there is amarked leveling of the rate profile associated with these internal cycloadditions when compared with their bimolecular counterparts.The high degree of order already present in the transition state for these intramolecular nitrile imine cycloadditions could account for the leveling of the rate profile.