The development of nitrogen-protecting groups that are orthogonal to the N-benzyl group for use in cross-bridged tetraazamacrocycles and the synthesis and complexation of bridged bis-tetraazamacrocycles are presented. The allyl, p-methoxybenzyl (PMB), and 2-naphthylmethyl (Nap) nitrogen-protecting groups were investigated for use on cross-bridged tetraazamacrocycle systems and conditions for deprotection were found for the N-allyl and N-PMB protecting groups. The conditions applied for the cleavage of the N-allyl and N-PMB groups and the systems that these conditions were employed on are illustrated below. This research has demonstrated that the N-allyl and N-PMB protecting groups are applicable to a variety of systems. These protecting groups have the potential to be utilized in the synthesis of novel cross-bridged bis-tetraazamacrocycles where the N-benzyl protecting group may not be applicable. These cross-bridged systems can be further functionalized, in particular the mono-benzyl cross-bridged cyclam system 33, for a variety of biomedical purposes including positron emission tomography (PET) imaging.
The N-allyl protecting group was also used to synthesize a cross-bridged bis-cyclen 31 that can now be further functionalized for a variety of biomedical purposes. Copper (II) and zinc (II) complexes of 94a and 90 and the diamide cross-bridged bis-tehaazamacrocycle 105 were also synthesized. These bis-tetraazamacrocycle systems may find use as potential anti-HIV agents or for stem-cell mobilization.
","abstract_html":"<p>The development of nitrogen-protecting groups that are orthogonal to the N-benzyl group for use in cross-bridged tetraazamacrocycles and the synthesis and complexation of bridged bis-tetraazamacrocycles are presented. The allyl, p-methoxybenzyl (PMB), and 2-naphthylmethyl (Nap) nitrogen-protecting groups were investigated for use on cross-bridged tetraazamacrocycle systems and conditions for deprotection were found for the N-allyl and N-PMB protecting groups. The conditions applied for the cleavage of the N-allyl and N-PMB groups and the systems that these conditions were employed on are illustrated below. This research has demonstrated that the N-allyl and N-PMB protecting groups are applicable to a variety of systems. These protecting groups have the potential to be utilized in the synthesis of novel cross-bridged bis-tetraazamacrocycles where the N-benzyl protecting group may not be applicable. These cross-bridged systems can be further functionalized, in particular the mono-benzyl cross-bridged cyclam system 33, for a variety of biomedical purposes including positron emission tomography (PET) imaging.</p><p>The N-allyl protecting group was also used to synthesize a cross-bridged bis-cyclen 31 that can now be further functionalized for a variety of biomedical purposes. Copper (II) and zinc (II) complexes of 94a and 90 and the diamide cross-bridged bis-tehaazamacrocycle 105 were also synthesized. These bis-tetraazamacrocycle systems may find use as potential anti-HIV agents or for stem-cell mobilization.</p>","abstract_has_math":false,"creators":["Young, Matthew J"],"institution":null,"degree_name":"Doctor of Philosophy","degree_level":"Dissertation","degree_discipline":null,"degree_department":null,"school":null,"contributors":["Gary R Weisman"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2009,"date_issued":"2009-01-01T08:00:00Z","date_published":"2009-01-01T08:00:00Z","updated_at":"2026-07-24T05:22:36Z","subjects":["Chemistry","Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://scholars.unh.edu/dissertation/613","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Gary R Weisman"]},{"key":"dc:creator","label":"Author","values":["Young, Matthew J"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Doctor of Philosophy"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry","Organic"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://scholars.unh.edu/dissertation/613"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The development of nitrogen-protecting groups that are orthogonal to the N-benzyl group for use in cross-bridged tetraazamacrocycles and the synthesis and complexation of bridged bis-tetraazamacrocycles are presented. The allyl, p-methoxybenzyl (PMB), and 2-naphthylmethyl (Nap) nitrogen-protecting groups were investigated for use on cross-bridged tetraazamacrocycle systems and conditions for deprotection were found for the N-allyl and N-PMB protecting groups. The conditions applied for the cleavage of the N-allyl and N-PMB groups and the systems that these conditions were employed on are illustrated below. This research has demonstrated that the N-allyl and N-PMB protecting groups are applicable to a variety of systems. These protecting groups have the potential to be utilized in the synthesis of novel cross-bridged bis-tetraazamacrocycles where the N-benzyl protecting group may not be applicable. These cross-bridged systems can be further functionalized, in particular the mono-benzyl cross-bridged cyclam system 33, for a variety of biomedical purposes including positron emission tomography (PET) imaging.
The N-allyl protecting group was also used to synthesize a cross-bridged bis-cyclen 31 that can now be further functionalized for a variety of biomedical purposes. Copper (II) and zinc (II) complexes of 94a and 90 and the diamide cross-bridged bis-tehaazamacrocycle 105 were also synthesized. These bis-tetraazamacrocycle systems may find use as potential anti-HIV agents or for stem-cell mobilization.
"]},{"key":"dc:title","label":"Title","values":["Development of nitrogen protecting groups and synthesis and complexation of bridged bis-tetraazamacrocycles"]}]}],"canonical_facts":{"dc:contributor":["Gary R Weisman"],"dc:creator":["Young, Matthew J"],"dc:description.abstract":["The development of nitrogen-protecting groups that are orthogonal to the N-benzyl group for use in cross-bridged tetraazamacrocycles and the synthesis and complexation of bridged bis-tetraazamacrocycles are presented. The allyl, p-methoxybenzyl (PMB), and 2-naphthylmethyl (Nap) nitrogen-protecting groups were investigated for use on cross-bridged tetraazamacrocycle systems and conditions for deprotection were found for the N-allyl and N-PMB protecting groups. The conditions applied for the cleavage of the N-allyl and N-PMB groups and the systems that these conditions were employed on are illustrated below. This research has demonstrated that the N-allyl and N-PMB protecting groups are applicable to a variety of systems. These protecting groups have the potential to be utilized in the synthesis of novel cross-bridged bis-tetraazamacrocycles where the N-benzyl protecting group may not be applicable. These cross-bridged systems can be further functionalized, in particular the mono-benzyl cross-bridged cyclam system 33, for a variety of biomedical purposes including positron emission tomography (PET) imaging.
The N-allyl protecting group was also used to synthesize a cross-bridged bis-cyclen 31 that can now be further functionalized for a variety of biomedical purposes. Copper (II) and zinc (II) complexes of 94a and 90 and the diamide cross-bridged bis-tehaazamacrocycle 105 were also synthesized. These bis-tetraazamacrocycle systems may find use as potential anti-HIV agents or for stem-cell mobilization.
"],"dc:identifier":["https://scholars.unh.edu/dissertation/613"],"dc:subject":["Chemistry","Organic"],"dc:title":["Development of nitrogen protecting groups and synthesis and complexation of bridged bis-tetraazamacrocycles"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Doctor of Philosophy"]},"updated_at":"2026-07-24T05:22:36Z"}